Novel isatin-indole derivatives as potential inhibitors of chorismate mutase (CM): Their synthesis along with unexpected formation of 2-indolylmethylamino benzoate ester under Pd-Cu catalysis

Gangireddy Sujeevan Reddy, Kazi Amirul Hossain, Jetta Sandeep Kumar, B. Thirupataiah, Rebecca Kristina Edwin, Varadaraj Bhat Giliyaru, Raghu Chandrashekhar Hariharapura, G. Gautham Shenoy, Parimal Misra, Manojit Pal

Research output: Contribution to journalArticle

Abstract

A series of novel isatin-indole derivatives has been designed as potential inhibitors of chorismate mutase (CM) that is known to be present in bacteria, fungi and higher plants but not in human. The design was supported by in silico docking studies that predicted strong interactions of these molecules with CM. The target compounds were synthesized via the one-pot coupling/cyclization method involving the reaction of an isatin based terminal alkyne with 2-iodosulfanilides under Pd-Cu catalysis. A number of isatin-indole derivatives were prepared using this method. A side product e.g. 2-indolylmethylamino benzoate ester derivative was obtained as a result of isatin ring opening (ethanolysis) of products in certain cases. Additionally, regioselective reduction of selected compounds afforded the corresponding C-3 hydroxy derivatives. All isatin-indole derivatives showed good to high inhibition of CM in vitro among which two compounds (3e and 3f) showed inhibition at nanomolar concentration.

Original languageEnglish
Pages (from-to)289-297
Number of pages9
JournalRSC Advances
Volume10
Issue number1
DOIs
Publication statusPublished - 01-01-2019

Fingerprint

Chorismate Mutase
Isatin
Benzoates
Catalysis
Esters
Derivatives
Alkynes
Cyclization
Fungi
Bacteria
indole
Molecules

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Reddy, Gangireddy Sujeevan ; Hossain, Kazi Amirul ; Kumar, Jetta Sandeep ; Thirupataiah, B. ; Edwin, Rebecca Kristina ; Giliyaru, Varadaraj Bhat ; Chandrashekhar Hariharapura, Raghu ; Shenoy, G. Gautham ; Misra, Parimal ; Pal, Manojit. / Novel isatin-indole derivatives as potential inhibitors of chorismate mutase (CM) : Their synthesis along with unexpected formation of 2-indolylmethylamino benzoate ester under Pd-Cu catalysis. In: RSC Advances. 2019 ; Vol. 10, No. 1. pp. 289-297.
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Novel isatin-indole derivatives as potential inhibitors of chorismate mutase (CM) : Their synthesis along with unexpected formation of 2-indolylmethylamino benzoate ester under Pd-Cu catalysis. / Reddy, Gangireddy Sujeevan; Hossain, Kazi Amirul; Kumar, Jetta Sandeep; Thirupataiah, B.; Edwin, Rebecca Kristina; Giliyaru, Varadaraj Bhat; Chandrashekhar Hariharapura, Raghu; Shenoy, G. Gautham; Misra, Parimal; Pal, Manojit.

In: RSC Advances, Vol. 10, No. 1, 01.01.2019, p. 289-297.

Research output: Contribution to journalArticle

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AU - Thirupataiah, B.

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AU - Giliyaru, Varadaraj Bhat

AU - Chandrashekhar Hariharapura, Raghu

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AU - Misra, Parimal

AU - Pal, Manojit

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