Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies

Bathula, Chandramohan; Dangi, Poonam; Hati, Santanu; Agarwal, Rahul; Munshi, Parthapratim; Singh, Ashutosh; Singh, Shailja; Sen, Subhabrata

doi:10.1039/c5nj01858g

Cited by 22 publications

(10 citation statements)

References 50 publications

(2 reference statements)

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“…It is noteworthy that current chemotherapeutic agents present low effectiveness due to the development of multidrug resistant cancers, while they display severe side effects (Bian et al, ; Mansoori, Mohammadi, Davudian, Shirjang, & Baradaran, ; Senapati, Mahanta, Kumar, & Maiti, ). Therefore, target identification and searching for new anticancer drugs endowed with cytotoxic activity is of great importance, while plant‐derived heterocyclic compounds and their derivatives have always consisted an invaluable source for the discovery of new therapeutic agents (Bathula et al, ; Demir, Özen, Ünlüsoy, Öztürk, & Bozdağ‐Dündar, ; Hati et al, ). Interestingly, heterocyclic scaffolds such as coumarins have a tremendous ability to regulate diverse range of cellular pathways, thus they can be regarded as key structures for multi‐targeting purposes (Thakur, Singla, & Jaitak, ).…”

Section: Introductionmentioning

confidence: 99%

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Kavetsou

Katopodi

Argyri

et al. 2020

Drug Development Research

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Eighteen 3-aryl-5-substituted-coumarins-six 5-acetyloxy-derivatives, six 5-hydroxyderivatives, and six 5-geranyloxy-derivatives-were synthesized, structurally characterized and their antioxidant activity, lipoxygenase inhibitory ability, as well as their cytotoxic activity against human neuroblastoma SK-N-SH and HeLa adenocarcinoma cell lines were evaluated. The 5-acetyloxy-compounds 3a-3f were found to be the best cytotoxic agents among all the compounds studied. The bromo-substituted coumarins 3a and 3b were remarkably active against HeLa cell line showing IC 50 1.8 and 6.1 μM, respectively. Coumarin 5e possessing a geranyloxy-chain on position 5 of the coumarin scaffold presented dual bioactivity, while 5-geranyloxy-coumarin 5f was the most competent soybean lipoxygenase inhibitor of this series (IC 50 10 μM). As shown by in silico docking studies, the studied molecules present allosteric interactions with soybean lipoxygenases.

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Section: Introductionmentioning

confidence: 99%

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Kavetsou

Katopodi

Argyri

et al. 2020

Drug Development Research

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“…A preliminary screening of a variety of heterocycles such as A → J (Figure ) prepared inhouse (Bathula, Dangi, et al, ; Bathula, Mamidala, et al, ; Bathula et al, ; Hati, Dutta, Dutta, Munshi, & Sen, ; Hati & Sen, ) against E. coli , B. subtilis , S. epidermidis , K. pneumonia , S. faecalis , and S. aureus provided a benzimidazole based molecule J , as the most potent against these pathogens, especially S. aureus (MIC: 7 μg/mL), where Amikacin was used as a positive control (Figure ). This result prompted us to synthesize a library of molecules based on benzimidazole via an unique oxone catalyzed oxidative distortion of quinazolines.…”

Section: Discussionmentioning

confidence: 99%

Transcriptome analysis predicts mode of action of benzimidazole molecules against Staphylococcus aureus UAMS‐1

Chauhan

Hati

Priyadarshini

et al. 2019

Drug Development Research

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Antimicrobial drug resistance is one of the most critical problems that plagued the human race in modern times. Discovery of novel antibiotics is important to counter this threat. Accordingly, herein we have reported the discovery of substituted benzimidazole class of molecules with antimicrobial property (specifically against Staphylococcus aureus). They were initially identified through a random screening and a novel catalytic synthetic strategy was utilized to access them.in vitro screening and phenotypic profiling revealed the antimicrobial nature. De novo transcriptome and gene analyses predicted the putative targets. This work provides a solid foundation for developing the benzimidazoles as a target specific antimicrobial preclinical candidate. K E Y W O R D S benzimidazole, de novo transcriptome analysis † Deepika Chauhan, Santanu Hati contributed equally to this study.

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“…There are examples of the formation of a spiro carbon center upon rearrangement of heterocyclic compounds [289–291] . 3‐Aroylpyrrolobenzoxazepinetriones 303a or 303b reacted with 2‐aminobenzenethiol to afford spiro‐fused benzothiazine‐pyrrolediones 304a or 304b .…”

Section: Synthesis Of Spirocyclic Quinoxaline Acridine Benzoxazinementioning

confidence: 99%

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

Гатауллин

2020

Helvetica Chimica Acta

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The review covers the results of studies published in the literature on the synthesis of spiro-linked heterocycles of the indole, quinoline, benzoxazine, benzothiazine, indenoquinoxaline, pyridopyrimidine, and acridine series. Possible approaches to the synthesis of spirocycles through a sequence of well-known Knoevenagel, Michael reactions, deamination cyclization of 1,2-dicarbonyl, CH-acid compounds, direct cycloaddition of activated olefins to isatins, 3-alkylideneindoles, 2-oxindoles, in situ generated azomethine ylides, indenoquinoxalines are analyzed. Attention is drawn to approaches to the preparation of spiro-fused compounds using reactions of intra-and intermolecular dearomatization of indoles. Recent advances in the synthesis of spiro-linked benzo heterocycles from derivatives of 2-olefin substituted anilines are summarized. The examples of the synthesis of spiro-fused heterocycles by means of metal complexes catalyzed decomposition of diazo compounds are given. Some syntheses of biologically active representatives are shown, as well as the use of transformations of spiroheterocycles in the preparation of other heterocycles.

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Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies

Abstract: A toolkit of indole scaffolds inspired from natural products.

Cited by 22 publications

References 50 publications

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Novel 3‐aryl‐5‐substituted‐coumarin analogues: Synthesis and bioactivity profile

Transcriptome analysis predicts mode of action of benzimidazole molecules against Staphylococcus aureus UAMS‐1

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

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