Discovery of tetrahydrocarbazoles as dual pERK and pRb inhibitors

Kulkarni, Mahesh R.; Mane, Madhav S.; Ghosh, Usha; Sharma, Rajiv; Lad, Nitin P.; Srivastava, Ankita; Kulkarni-Almeida, Asha; Kharkar, Prashant S.; Khedkar, Vijay M.; Pandit, S. S.

doi:10.1016/j.ejmech.2017.02.062

Cited by 13 publications

(8 citation statements)

References 31 publications

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“…Furthermore,t his methodology is also applicable to the cyclization of indoles,a sillustrated with the high-yielding conversion of 19 into 20 ( Figure 5), which was used as ap recursor of ad ual inhibitor of kinase phosphorylation. [19] To gain an insight into the mechanism of the iridiumcatalyzed reaction, we turned to deuterium labelling (Figure 6a) /k D = 1.0). These result suggest that in the presence of the catalyst, the sulfoxonium ylide would give carbene VIII,a nd this intermediate could undergo an ucleophilic attack to give IX,t hat would in turn undergo rapid 1,2-deuterium migration to give X,b efore af inal elimination to XI and its facile rearomatization to the observed product, accompanied by intra-and intermolecular scrambling of the deuterium label (Figure 6b).…”

Section: Angewandte Chemiementioning

confidence: 99%

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Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

et al. 2019

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The functionalization of aryl and heteroaryls using α‐carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α‐carbonyl sulfoxonium ylides onto benzenes, benzofurans and N‐p‐toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles and N‐methyl indoles undergo cyclization in the presence of an iridium catalyst. Significantly, these two sets of conditions are chemospecific for each groups of substrates.

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Section: Angewandte Chemiementioning

confidence: 99%

“…Furthermore, this methodology is also applicable to the cyclization of indoles, as illustrated with the high‐yielding conversion of 19 into 20 (Figure ), which was used as a precursor of a dual inhibitor of kinase phosphorylation …”

Section: Figurementioning

confidence: 99%

Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls

et al. 2019

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“…It focused on the synthesis and antimicrobial activity of compounds produced by combining two biologically active compounds (NSAIDS and THCZ). THCZ and Carbazole ring scaffolds are present in some alkaloids [2], they have a variety of biological effects such as antiviral (3) , antitumor (4) , antibacterial (5,6) and broad-spectrum antifungal activity [7,8]. NSAIDs are considered as non-antibiotic drugs reported to display antibacterial activity [9], Some NSAIDs such as indomethacin and diclofenac have been shown to have synergistic effect with particular antimicrobial drugs [10].…”

Section: Introductionmentioning

confidence: 99%

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2022

J. Med. Chem. Sci.

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New 6-chloro-1,2,3,4-tetrahydrocarbazole compounds were prepared from the reaction of cyclohexanone with 4-chlorophenylhydrazine. The synthesis of heterocyclic compounds was carried out through the reaction of cyclohexanone with 4-chlorophenylhydrazine, then the produced compound was treated with two NSAIDs (indomethacin, diclofenac) by amide bond formation to form N-substituted THCZ by NSAIDs. The characterization of prepared compounds was identified using the 1 H, 13 C NMR and FT-IR spectroscopies. The antimicrobial activity of the synthesized compounds was tested in vitro to discover a good activity as antifungal and moderate as antibacterial, which was confirmed by the docking study of the compounds.

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“… 18 Indole-3-acetic acid (IAA) is an important phytohormone, 19 and thaxtomin A shows effective weed control ability and exerts no toxicity to rice. 20 Moreover, tetrahydrocarbazole is a well-known privileged scaffold, 21 possessing many different biological functions such as anti-tumor, 22 antibiotics 23 and anti-virus. 24 Tetrahydrocarbazole also shows photosynthesis–inhibitory activity and acts as a herbicide prototype.…”

Section: Introductionmentioning

confidence: 99%