Dr HARDESH K MAURYA

Quinone

2024-09-19T23:42:00.000-07:00

Quinones are a class of cyclic organic compounds characterized by their conjugated double-bond systems and a distinct chemical reactivity. The history of quinone can be traced back to the early 19th century, when chemists began to understand the structures and properties of these compounds.

Early Discoveries

1826: The term "quinone" derives from "quinine," the alkaloid first isolated from the bark of the cinchona tree. The discovery of quinine itself in the 17th century by Jesuit missionaries in South America paved the way for subsequent studies into related compounds.
1833: The first true quinone, 1,4-benzoquinone, was synthesized by the chemist August Wilhelm von Hofmann. He extracted it from coal tar, marking a significant step in organic chemistry.

Structural Elucidation

1850s-1860s: Further advancements were made by chemists like Adolf von Baeyer and Hermann Emil Fischer, who studied the properties and reactions of quinones. Their work laid the foundation for understanding the electronic structure and reactivity of these compounds.
1860: The structural formula of quinone was proposed, and it became evident that quinones could be derived from aromatic compounds through oxidation.

Expanding Knowledge

20th Century: The chemical industry began to recognize the importance of quinones in various applications. They were found to be useful as dyes, pigments, and in pharmaceuticals. Quinones played a key role in the development of synthetic dyes and eventually in the field of biochemistry, where they were identified as intermediates in metabolic pathways.

Modern Applications

1970s-Present: Quinones have gained attention in the fields of materials science and medicine. Their unique redox properties make them valuable in electronic applications, such as in organic solar cells and batteries.
Biochemistry: Quinones are now known to be important in biological systems, particularly in photosynthesis and cellular respiration, where they participate as electron carriers.

Conclusion

The study of quinones has evolved significantly from their initial discovery to their current applications in various scientific fields. Their unique chemical properties and biological significance continue to make them a topic of interest for researchers today.

Benzoquinone

2024-09-19T23:38:00.000-07:00

Benzoquinone is an organic compound with a rich history, pivotal in organic chemistry and various applications. Here’s an overview of its development:

Early Discoveries

Benzoquinone is derived from benzene, with its earliest forms identified in the mid-19th century. The compound is characterized by a six-membered aromatic ring with two ketone groups, existing mainly as 1,2-benzoquinone (ortho-quinone) and 1,4-benzoquinone (para-quinone).

19th Century

The isolation of benzoquinone compounds began in the 1830s. Researchers such as Charles Frédéric Gerhardt explored quinones' chemical properties, leading to increased interest in their structure and reactivity. The understanding of their roles in oxidation-reduction reactions was foundational in developing organic chemistry.

Chemical Structure and Types

Benzoquinone's structure, with its unique arrangement of double bonds and carbonyl groups, allows for a variety of reactions, including electrophilic substitutions and polymerizations. The identification of ortho- and para-quinones added depth to their chemical properties, influencing subsequent synthetic approaches.

20th Century Applications

In the 20th century, the synthesis of benzoquinone and its derivatives expanded significantly. Its utility in dyes, particularly in the textile industry, was notable. Benzoquinones became key intermediates in the production of various synthetic dyes due to their vibrant colors and stability.

Biological Significance

Benzoquinones also gained attention for their biological activities. They are involved in the biosynthesis of natural products and play roles in photosynthesis

Naphthoquinone

2024-09-19T23:36:00.000-07:00

Naphthoquinone is an organic compound that has a fascinating history tied to its discovery, synthesis, and applications.

Early Discoveries

Naphthoquinones are derivatives of naphthalene and are characterized by a fused ring structure containing two ketone groups. The discovery of naphthalene itself dates back to the early 19th century, when it was isolated from coal tar. The exploration of its derivatives led to the identification of naphthoquinones in the mid-1800s, with scientists investigating their chemical properties and potential uses.

Chemical Structure and Types

Naphthoquinones primarily exist in two forms: 1,2-naphthoquinone and 1,4-naphthoquinone. The distinction lies in the positioning of the carbonyl groups. 1,4-naphthoquinone, in particular, gained attention due to its role in biological systems, notably in the synthesis of vitamin K and its involvement in various biochemical pathways.

20th Century Developments

In the 20th century, advancements in organic chemistry allowed for the synthesis of naphthoquinones, which spurred interest in their applications. Researchers began exploring their use in dyes, pharmaceuticals, and as intermediates in chemical reactions. The compound's unique properties, including its redox activity, also made it a candidate for applications in electrochemistry and materials science.

Biological Significance

Naphthoquinones have been recognized for their biological significance. For instance, 1,4-naphthoquinone is essential in the biosynthesis of vitamin K, a vital nutrient for blood coagulation. Moreover, certain naphthoquinones, like menadione (vitamin K3), have been studied for their potential anticancer properties and as antibacterial agents.

Contemporary Research

Today, naphthoquinones are subjects of ongoing research in various fields, including medicinal chemistry and environmental science. Their roles in natural products and as precursors in the synthesis of complex molecules are of particular interest. Researchers are also investigating their potential in nanotechnology and as dyes in solar cells.

Conclusion

The history of naphthoquinone reflects a journey from early chemical exploration to modern applications in health and technology. As research continues, the potential of these compounds may lead to new discoveries and innovations in various scientific disciplines.

PHARMACEUTICAL ORGANIC CHEMISTRY-II (Theory & Practical)

2021-02-09T09:22:00.000-08:00

www.notionpress.com

Synthesis, photophysical and anticancer study of D-ring extended estrone analogues

2020-11-14T18:57:00.001-08:00

RSC Advances 2015, 5, 68843-68851

Hardesh K. Mauryaa, Mohammad Hasanainb, Ch. Pavan Kumarc, Prema G. Vasudevad, Jayanta Sarkarb, M. Chandrasekharamc and Atul Gupta*a

A concise route for the highly substituted ring extended estrone derivatives has been established. This protocol involves very simple, facile and one step ring transformation and cyclization process. The preliminary absorption, emission spectroscopic and biological studies of these compounds revealed the possible use of such prototypes in cancer chemotherapy as fluorescence probes.

Crystal structures of four [delta]-keto esters and a Cambridge Structural Database analysis of cyano-halogen interactions

2015-10-28T09:56:00.001-07:00

K. Kamal, H. K. Maurya, A. Gupta and P. G. Vasudev

RESEARCH PAPERS
Acta Cryst. (2015). C71, 921-928
doi:10.1107/S2053229615017106

The revived interest in halogen bonding as a tool in pharmaceutical cocrystals and drug design has indicated that cyano-halogen interactions could play an important role. The crystal structures of four closely related -keto esters, which differ only in the substitution at a single C atom (by H, OMe, Cl and Br), are compared, namely ethyl 2-cyano-5-oxo-5-phenyl-3-(piperidin-1-yl)pent-2-enoate, C19H22N2O3, (1), ethyl 2-cyano-5-(4-methoxyphenyl)-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C20H24N2O4, (2), ethyl 5-(4-chlorophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21ClN2O3, (3), and the previously published ethyl 5-(4-bromophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21BrN2O3, (4) [Maurya, Vasudev & Gupta (2013). RSC Adv. 3, 12955-12962]. The molecular conformations are very similar, while there are differences in the molecular assemblies. Intermolecular C-HO hydrogen bonds are found to be the primary interactions in the crystal packing and are present in all four structures. The halogenated derivatives have additional aromatic-aromatic interactions and cyano-halogen interactions, further stabilizing the molecular packing. A database analysis of cyano-halogen interactions using the Cambridge Structural Database [CSD; Groom & Allen (2014). Angew. Chem. Int. Ed. 53, 662-671] revealed that about 13% of the organic molecular crystals containing both cyano and halogen groups have cyano-halogen interactions in their packing. Three geometric parameters for the C-XNC interaction (X = F, Cl, Br or I), viz. the NXdistance and the C-XN and C-NX angles, were analysed. The results indicate that all the short cyano-halogen contacts in the CSD can be classified as halogen bonds, which are directional noncovalent interactions.

Natural and Synthetic Molecular Medicine in Cancer Research: A Review

2015-03-16T05:01:00.001-07:00

Journal of Cancer Research and Molecular Medicine

Volume 1, Issue 1 - 2014

© Hardesh K Maurya 2014

www.opensciencepublications.com

PDF Download link

Review Article

Hardesh K Maurya*

Medicinal Chemistry Department, CSIR-Central Institute of Aromatic and Medicinal Plants, Picnic Spot road,

Lucknow-226015, India

Abstract

This review presents the stimulating area of natural and synthetic anticancer drugs which are presently used for the cure of various type of cancer. In this review, twenty one naturally, semisynthetic naturally occurring and 109 synthetic anticancer drugs are reported. The emphasis of this review has described related structure, mechanism of action and major disadvantage of these drugs with the aims of providing an overview of anticancer drugs. This review will be provide current status of cancer drug and helpful to make strategy in the

search of novel anticancer molecular medicine in future.

Keywords: Anticancer drugs; Chemotherapy; Cancer; Carcinoma; Tumor; Cancer medicine

Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles “in H2O”

2014-09-30T07:57:00.001-07:00

- - Tetrahedron Letters, In Press, Accepted Manuscript, Available online 28 September 2014
Vishnu K. Tandon,
Manoj K. Verma,
Hardesh K. Maurya,
Sandeep Kumar
- Received 23 July 2014, Revised 20 September 2014, Accepted 22 September 2014, Available online 28 September 2014
  DOI: 10.1016/j.tetlet.2014.09.103
  
  Abstract
  
  An efficient, novel and concise one pot regio- and chemoselective synthesis of benzo[a]phenazines (4) and naphtho[2,3-d]imidazoles (8) has been accomplished in excellent yields by nucleophilic substitution reaction of 2,3-dichloro-1,4-naphthoquinone (1) with o-phenylenediamine (2) and benzamidines (7) respectively “in H₂O” using base and micelles (SDS) as catalyst. Analogues reaction of 2,3-dichloro-1,4-naphthoquinone (1) with 2-aminobenzenethiol (9) under identical conditions led to formation of a mixture of benzo[b]phenothiazine (10), benzo[a]phenothiazine (11) and benzo[a]-1,4-benzothiazino-3,2-phenothiazine (12) in 17, 23 and 57% yields respectively.

Boron tribromide mediated C-C bond formation in cyclic ketones: a transition metal free approach

2014-05-13T09:07:00.003-07:00

Imran Ahmad, Vinay Pathak, Prema G Vasudev, Hardesh K. Maurya and Atul Gupta

RSC Adv. 2014, 4, 24619

DOI: 10.1039/C4RA01745E

Received 27 Feb 2014,

Accepted 12 May 2014

First published online 13 May 2014

Abstract

Borontribromide (BBr3) is a well known demethylating agent. Current investigation was focused on a new application of borontribromide as C-C bond forming agent in cyclic ketones. In this study, borontribromide mediated C-C bond formation reactions of tetralones, chromenone, thiochromenone and indanones were explored. Methoxy group containing ketones showed selective C-C bond formation reaction instead of demethylation of methoxy group. MM2 steric energy calculations for final products showed that reaction favored the formation of exo or endo cyclic double bond containing products depending upon their low MM2 steric energy in a specific frame structure as observed in x-ray crystallography. A comprehensive crystallographic and pi-stacking analysis of product 10a exhibited the formation of 10a as enantiomeric mixture and its centre of inversion was stabilized by a set of three unique pi-pi interactions.

A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs

2014-05-07T08:27:00.004-07:00

Hardesh K. Maurya and Atul Gupta

RSC Adv., 2014, 4, 22106-22114

DOI: 10.1039/C4RA01689K

Received 26 Feb 2014,
Accepted 02 May 2014
First published online 07 May 2014

Abstract
The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds had further been explored for the synthesis of diversified pyrimidines 4, 6-8, 11-12 and 14 through sequential approach.

Regioselective synthesis of polycyclic aza-oxa and aza-oxa-thia heteroarenes as Colo-205 and HepG2 carcinoma cells growth inhibitors

2014-05-05T08:41:00.001-07:00

European Journal of Medicinal Chemistry,Volume 81, 23 June 2014, Pages 367–377 Available online 5 May 2014
Hardesh K. Maurya, Sanjay K. Gautam, Ramendra Pratap, Vishnu K. Tandon, Abhinav Kumar, Brijesh Kumar, Shruti Saxena, Deepti Tripathi, Meenakshi Rajwanshi, Mukul Das, Vishnu Ji Ram

DOI: http://dx.doi.org/10.1016/j.ejmech.2014.05.013

Abstract

An efficient regioselective synthesis of polycyclic diheteroaryl[b,d]pyrans and diheteroaryl[c,e][1,2]diazepines has been reported through ring transformation reactions of 2-oxo-2,5-dihydrothiochromeno[4,3-b]pyrans (3,4), 2-oxo-5,6-dihydro-2H-benzo[b]pyrano[2,3-d]oxepine/thiepine (8, 9) and 6-oxo-3,6-dihydro-2H-naphtho[1,2-b]pyrano[2,3-d]oxepine (15) by hydrazine, at ambient and reflux temperature. Nine compounds viz 5a,b; 10a,c,d; 12b; 13b; 16 and 1-methylthio-5,6-dihydrobenzo[f]quinoline (0.1-100 μM) were screened for their cytotoxicity in normal (IEC-6), carcinoma (Colo-205) and Hep G2 cell lines. None of the compounds showed cytotoxicity in normal IEC-6 cells while 10a,d and 16 resulted in killing of Colo-205 cells with IC₅₀ ranging between 20-60μM while 10c and 13b caused killing of HepG2 cells with IC₅₀ values ranging between 60-80 μM concentration. Further, 10a,d and 16 caused apoptosis through a cascade of mitochondrial pathway in Colo-205 cells indicating anticancerous potential against intestinal cancer. Interestingly, compounds 10c and 13b exhibited apoptosis through mitochondrial pathway in HepG2 cells suggesting anticancer activity against hepatic cancer.

Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1H-pyrazoles as anti-tubercular agents

2014-05-05T08:35:00.001-07:00

Bioorganic & Medicinal Chemistry Letters, Volume 24, Issue 13, 1 July 2014, Pages 2892–2896, Available online 4 May 2014
Vinay Pathak, Hardesh K. Maurya, Sandeep Sharma, Kishore K Srivastava, Atul Gupta

DOI: http://dx.doi.org/10.1016/j.bmcl.2014.04.094

Abstract

Various substituted 4,6-diarylpyrimidin-2-amine (4), 4,6-diaryl-2-(heteroaryl)pyrimidine (6) and 1-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)ethanone (7) derivatives were synthesized in good yields using simple methodology. The synthesized compounds (4-7) were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain. Compounds 4a, 6b, 7b, and 7c exhibited significant anti-tubercular activity at MIC values 25, 25, 12.5 and 12.5 μM concentration. In vitro cytotoxicity data using non cancerous hepatic monocytes (THP-1) cells indicated that most active compounds 7b and 7c were safe as their MIC values were much lower than their cytotoxic values

Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells

2014-02-20T08:05:00.003-08:00

Vishnu K. Tandon, Hardesh K. Maurya, Sandeep Kumar, Aijaz Rashid and Dulal Panda

RSC Adv., 2014, 4, 12441-12447

Full TextDOI: 10.1039/C3RA47720G
This article describes the preparation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells. We have identified three most active naphthoquinones 10, 12 and 15 that potently induce apoptosis in human cervical carcinoma (HeLa) cells. One of these three compounds perturbed both microtubule and actin filaments.

A carbanion induced synthesis of highly congested pyrazole and imidazole containing heterocycles

2014-02-03T23:40:00.000-08:00

Tetrahedron Letters, Volume 55, Issue 10, 5 March 2014, Pages 1715-1719
Hardesh K Maurya, Atul Gupta
Medicinal Chemistry Department, Central Institute of Medicinal and Aromatic Plants, P.O. CIMAP, Kukrail Road, Lucknow-226015, India
http://dx.doi.org/10.1016/j.tetlet.2014.01.095

Abstract

An efficient approach to the synthesis of highly congested di, penta and hexacyclic pyrazoles as well as imidazole fragment containing novel heterocyclic molecule has been developed through a carbanion induced transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans. Due to the presence of fluorescence, we report their prime application metal sensor as off/on switching in ferric ions.

Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents

2013-09-07T10:16:00.001-07:00

Bioorganic & Medicinal Chemistry Letters, Volume 23, Issue 21, 1 November 2013, Pages 5844–5849, Available online 5 September 2013
Hardesh K. Maurya, Ruby Verma, Saba Alam, Shweta Pandey, Vinay Pathak, Sandeep Sharma, Kishore K. Srivastava, Arvind S. Negi, Atul Gupta
http://dx.doi.org/10.1016/j.bmcl.2013.08.101
Abstract

Various substituted 5,6-dihydro-8-methoxybenzo[h]quinazolin-2-amine, 1-(3-(4-alkoxyphenyl)-7-methoxy-3,3a,4,5-tetrahydro-2H benzo[g]indazol-2-yl)ethanone, pyrazole and 2,6-diarylpyridine derivatives have been synthesized in good yields by an efficient methodology. The synthesized compounds (4-23) were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain. Compounds 6a,6c, 8a, 19a and 19e exhibited significant anti-tubercular activity at MIC values 50, 100, 50, 25 and 100 μM concentration. In vitro cytotoxicity data using THP-1 cells indicated that most active compound 19a is safe as its MIC value is much lower than the cytotoxic value.

A Regio Selective Synthesis of 2,6-Diarylpyridines

2013-05-18T11:01:00.001-07:00

Hardesh K. Maurya, Prema G Vasudev and Atul Gupta

RSC Adv., 2013,3, 12955-12962

DOI: http://dx.doi.org/10.1039/C3RA41575A
A regio selective synthesis of 2,6-diarylpyridines through base (sodium hydroxide in DMSO) catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones with benzamide has been delineated. However, similar reaction of 2H-pyran-2-ones with benzamide using base sodium hydroxide in absolute ethanol have yielded highly congested delta keto esters with active methylene centre instead of 2,6-diarylpyridines.

A carbanion induced ring switching synthesis of spiranes an unprecedented approach

2012-08-25T11:09:00.000-07:00

Hardesh K. Maurya , Ramendra Pratap , Abhinav Kumar , Brijesh Kumar , Volker Huch , Vishnu K. Tandon and Vishnu Ji Ram

RSC Adv., 2012,2, 9091-9099

View Full text (RG),

DOI: 10.1039/C2RA21587J

An unique approach to the synthesis of heterocyclic spiranes through ring switching transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans has been developed. The spirane dimer 11d displayed interestinghalogen-hydrogen bonding to generate an elliptical cavity and may be relevant to the generation of a host guest assembly for specific cations and also a low helimerization energy barrier of spirane 17a.

A Diversified Approach to the Synthesis of Highly Functionalized Novel Azines and Azoles from 2H-Pyran-2-ones

2012-05-26T04:43:00.000-07:00

Heterocycles 2012, DOI: 10.3987/COM-12-S(N)1

Pushyamitra Mishra, Sandeep Kumar, Hardesh K. Maurya, Sanjay K. Gautam, Brijesh Kumar, Vishnu K. Tandon,* and Vishnu Ji Ram*

Abstract

One-pot regioselective synthesis of 2,6-diarylpyrimidines (4), 2,6-disubstituted pyridines (5 and 6), 5-aryl-3-cyanomethyl-1H-pyrazoles (7) through base catalyzed ring transformation of suitably functionalized 2H-pyran-2-ones by arylamidines, cyanamide, ammonium carbonate, hydrazines respectively has been developed. Our synthetic approach opened a new avenue for the regioselective synthesis of 2,6-diarylpyrimidines and 2,6-disubstituted pyridines and cyanomethylpyrazoles. The procedure is very simple, efficient and economically viable. The protocol provides an efficient methodology for the preparation of new class of medicinally useful and highly functionalized azines and azoles from single precursor 2H-pyran-2-ones.

Sequential approach to the synthesis of ‘U and Z’ shaped polycyclic heteroarenes

2012-03-25T09:13:00.000-07:00

Organic & Biomolecular Chemistry

Hardesh K. Maurya , Sanjay K Gautam , Ramendra Pratap , Vishnu K. Tandon , Abhinav Kumar , Vikas Bajpai , Brijesh Kumar and Vishnu Ji Ram

Org. Biomol. Chem., 2012, 10, 4977

DOI: 10.1039/C2OB25173FThe synthesis of three new classes of heteroarenes, built through the sequential fusion of naphthalene, benzo/naphtho[b]oxepine and thiochromene rings with pyran and pyrimidine ring system to give ‘U and Z’ shapes of structural frame work is reported. The methodology is based on the synthesis of pyran fused intermediates, 1-methylthio-3-oxo-5,6-dihydro-3H-benzo[f]chromene-2-carbonitrile (3), 4-methylthio-2-oxo-5,6-dihydro-2H-benzo/naphtho[b]pyrano[2,3-d]oxepine-3-carbonitriles (10, 20) and 4-methylthio-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles (15) from the reaction of 2-tetralone, benzo/ naphtho[b]oxepin-5-ones and thiochromen-4-ones with methyl 2-cyano-3,3-dimethylthioacrylate respectively. Further condensation of intermediates 3, 10, 20 and 15 with amidines led to the formation of tetracyclic ‘U’ shaped 4-amino-2-aryl-7,8-dihydro-5-oxo-5H-naphtho[2,1-b]pyrimido[4,5-d]pyrans (8) and ‘Z’ shaped 4-amino-2-aryl-5-oxo-12,13-dihydro-5H-benzo/naphtho[b]oxepino[5,4-b]pyrimido[4,5-d]pyrans (12, 22) and 4-amino-2-aryl-5-oxo-5,12-dihydrothiochromeno[4,3-b]pyrimido[4,5-d]pyrans (17). Compound 12f forms chain of dimers through N-H∙∙∙O interactions as indicated by the X-ray structure analysis and the quantum chemical calculations performed at the MP2 level indicates that this interaction energy is 10 kJ mol.-1

InBr3- and AgOTf-catalyzed Beckmann rearrangement of (E)-benzoheterocyclic oximes

2012-03-25T09:06:00.002-07:00

Journal of Heterocyclic Chemistry

Vishnu K. Tandon^*,
Anoop K. Awasthi,
Hardesh K. Maurya,
Pushyamitra Mishra

DOI: 10.1002/jhet.438

Beckmann rearrangement of (E)-4-chromanone oxime, (E)-5-oximino-3,4-dihydro-1(2H)-benzoxepines, and (E)-5-oximino-3,4-dihydro-1(2H)-benzothiepine are catalyzed by InBr₃ and AgOTf in refluxing acetonitrile resulting in the formation of pharmaceutically active heterocycles benzoxazepin-4-one, 5-oxo-benzoxazocines, and 5-oxo-benzothiazocine derivative, respectively, in excellent yield. J. Heterocyclic Chem., (2012).

Synthesis of thiophenes and pyranone fused thiophenes by base induced inter and intramolecular C–S and C–C bond formation: a non-catalytic approach

2012-03-25T09:03:00.001-07:00

Tetrahedron Letters

Volume 53, Issue 9, 29 February 2012, Pages 1056–1059

Pushyamitra Mishra,
Hardesh K. Maurya,
Brijesh Kumar,
Vishnu K. Tandon,
Vishnu Ji Ram

http://dx.doi.org/10.1016/j.tetlet.2011.12.066,

Abstract

An efficient and concise one pot synthesis of highly functionalized thiophenes and pyranone fused thiophenes has been delineated through base induced ring transformation of suitably functionalized 2H-pyran-2-ones by ethyl thioglycolate by inter and intramolecular C–S and C–C bond formation.

Non-catalytic approach to the synthesis of partially reduced ‘S’ shaped dioxathia-, and oxadithiahelicenes through base induced inter-, and intramolecular C–C bond formation

2011-09-08T10:44:00.000-07:00

Hardesh K. Maurya, Vishnu K. Tandon, Brijesh Kumar, Abhinav Kumar, Volker Hüch and Vishnu Ji Ram

Org. Biomol. Chem., 2012, 10, 605-613 DOI: 10.1039/C1OB06091K

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An efficient and convenient route for the construction of helical ‘S’ shaped dioxathia- and oxadithiahelicenes with oxygen and sulfur atoms located in the middle of the outer helix has been developed through base induced inter-, and intramolecular C-C bond formation from the reaction of 4-sec.amino-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles with 3,4-dihydro-2H-benzo[b]oxepin-5(2H)-ones, 3,4-dihydrobenzo[b]thiepin-5(2H)-one and thiochroman-4-ones separately. Quantum chemical calculations have also been carried out to explore the geometries and electronic structures of newly synthesized compounds to envisage the pathway for interconversion of both atropisomers. The determination of helicity parameters and configurational stability demonstrate that the energy barrier is strongly dependent on the nature of hetero atoms present.

Micelles catalyzed chemoselective synthesis ‘in water’ and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents

2011-09-07T11:25:00.000-07:00

Vishnu K.Tandon,Hardesh K. Maurya, Nripendra N. Mishra and Praveen K. Shukla

Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent) and TBAB, a phase transfer catalyst and evaluated for their in vitro antifungal and antibacterial activity. The antifungal profile of 3, 4a, 4b and 6 indicated that compounds 3a, 3b, 4b, 6a and 6c have potent antifungal activity compared to clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Sporothrix schenckii, Trichophyton mentagraphytes and Candida parapsilosis and compound 3b has been found to be a lead antifungal agent for further study.

Oxaheterocycles: Di- and Trioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-6,7-diones and Dibenzo[a,c]cycloheptene-3-carbonitriles

2011-07-15T09:50:00.000-07:00

Paper

Heterocycles Volume 84, Issue 1 DOI: 10.3987/COM-11-S(P)22

Hardesh K. Maurya, Ramendra Pratap, Vishnu K. Tandon, Pushyamitra Mishra, Brijesh Kumar, Vishnu Ji Ram

An efficient and convenient synthesis of 9-aryl-11,12-dihydro-13H-5,8-dioxabenzo[3,4]cyclohepta[1,2-a] naphthalene-6,7-diones and 9-aryl-11,12-dihydro-5,8,13-trioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-6,7-diones has been delineated through base catalyzed condensation-cyclization of 4-methylsulfanyl-2-oxo-2,5,6,7-tetrahydro-1-oxadibenzo[a,c]cycloheptene-3-carbonitriles and 4-methylsulfanyl-2-oxo-5,6-dihydro-2H-1,7-dioxadibenzo[a,c]cycloheptene-3-carbonitriles with aryl methyl ketone separately. We have also reported the synthesis of 2-aryl-4-sec-amino-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-3-carbonitriles through ring transformationof 4-sec-amino-2-oxo-2,5,6,7-tetrahydro-1-oxadibenzo[a,c]cycloheptene-3-carbonitriles with aryl methyl ketones in the presence of powdered KOH/NaOH in DMF. We have successfully synthesized 4-aryl-2-(piperidin-1-yl)-5,6-dihydro-7-oxadibenzo[a,c]cycloheptene-1-carbonitriles as isomeric products through ring transformation of 6-aryl-4-sec-amino-2H-pyran-2-one-3-carbonitriles by 3,4-dihydro-2H-benzo[b]oxepin-5(2H)-ones.

Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles

2010-06-28T00:46:00.001-07:00

Vishnu K. Tandon and Hardesh K. Maurya
Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles ‘on water’ is not facile. An unprecedented economical, green methodology approach using ordinary laundry detergent (LD; washing powder, 0.5 mol %, reusable)/SDS as surfactant ‘in water’ for nucleophilic substitution by oxygen nucleophiles in 1,4-quinones in excellent yields has been demonstrated.

Dr HARDESH K MAURYA

Quinone

Early Discoveries

Structural Elucidation

Expanding Knowledge

Modern Applications

Conclusion

Benzoquinone

Early Discoveries

19th Century

Chemical Structure and Types

20th Century Applications

Biological Significance

Naphthoquinone

Early Discoveries

Chemical Structure and Types

20th Century Developments

Biological Significance

Contemporary Research

Conclusion

PHARMACEUTICAL ORGANIC CHEMISTRY-II (Theory & Practical)

Synthesis, photophysical and anticancer study of D-ring extended estrone analogues

Crystal structures of four [delta]-keto esters and a Cambridge Structural Database analysis of cyano-halogen interactions

Natural and Synthetic Molecular Medicine in Cancer Research: A Review

Micelles catalyzed one pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles “in H2O”

Abstract

Boron tribromide mediated C-C bond formation in cyclic ketones: a transition metal free approach

A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs

Regioselective synthesis of polycyclic aza-oxa and aza-oxa-thia heteroarenes as Colo-205 and HepG2 carcinoma cells growth inhibitors

DOI: http://dx.doi.org/10.1016/j.ejmech.2014.05.013

Abstract

Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1H-pyrazoles as anti-tubercular agents

DOI: http://dx.doi.org/10.1016/j.bmcl.2014.04.094

Abstract

Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells

A carbanion induced synthesis of highly congested pyrazole and imidazole containing heterocycles

Abstract

Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents

A Regio Selective Synthesis of 2,6-Diarylpyridines

A carbanion induced ring switching synthesis of spiranes an unprecedented approach

A Diversified Approach to the Synthesis of Highly Functionalized Novel Azines and Azoles from 2H-Pyran-2-ones

Heterocycles 2012, DOI: 10.3987/COM-12-S(N)1

Abstract

Sequential approach to the synthesis of ‘U and Z’ shaped polycyclic heteroarenes

Organic & Biomolecular Chemistry

InBr3- and AgOTf-catalyzed Beckmann rearrangement of (E)-benzoheterocyclic oximes

Journal of Heterocyclic Chemistry

Synthesis of thiophenes and pyranone fused thiophenes by base induced inter and intramolecular C–S and C–C bond formation: a non-catalytic approach

Abstract

Non-catalytic approach to the synthesis of partially reduced ‘S’ shaped dioxathia-, and oxadithiahelicenes through base induced inter-, and intramolecular C–C bond formation

Micelles catalyzed chemoselective synthesis ‘in water’ and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents

Oxaheterocycles: Di- and Trioxabenzo[3,4]cyclohepta[1,2-a]naphthalene-6,7-diones and Dibenzo[a,c]cycloheptene-3-carbonitriles

Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles