RESEARCH ARTICLE

 

Synthesis and antimicrobial activity of novel 3-[1-(3-nitrophenyl)-ethyl]-1-(indole-1-yl) substituted aryl/alkyl-phosphinoyl/thiophosphinoyl/ selenophosphinoyl-1H-indole derivatives

 

 

Boppudi Hari Babu^I; M. Anil Kumar^I; Ch. Mohan^I; C. Naga Raju^{I, *}; B. Venu Babu^II; Ch. Chandi Maruti Kumari^III; Payala Anuradha^III

^IDepartment of Chemistry, Sri Venkateswara University, Tirupati-517 502, India
^IIDivïs Laboratories Ltd. (R&D), Sanath Nagar, Hyderabad-500 018, India
^IIIDepartment of Microbiology, Sri Padmavati Women's University, Tirupati-517 502, India

 

 

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ABSTRACT

Syntheses of novel 3-[1-(3-nitrophenyl)-ethyl]-1-(indole-1-yl) substituted aryl/alkyl phosphinoyl/thiophosphinoyl/ selenophosphinoyl-1H-indole derivatives were accomplished in two steps. The synthetic route involves the cyclisation of equimolar quantities of 3-[1H-3-indolyl(3-nitrophenyl)methyl]-1H-indole with dichlorophenyl phosphine/ethyldichlorophosphite in the presence of triethylamine in dry acetonitrile at room temperature. These compounds were further converted to the corresponding oxides, sulphides and selenides by reacting them with hydrogen peroxide, sulphur and selenium, respectively. The structures of the novel products were established by elemental analyses, IR, ¹H, ¹³C and ³¹P NMR and mass spectroscopy. They were screened for antibacterial and antifungal activity against Staphylococcus aureus/Klebsiella pneumoniae and Pellicularia solmanicolor/Macrophomina phaseolina, respectively.

Keywords: Bisindolylalkanes, alkyl/aryl phosphorodichloridates, antimicrobial activity

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Acknowledgements

The authors express thanks to Prof. C. Devendranath Reddy and Dr C. Suresh Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, India, for encouragement, and the Director, Indian Institute of Sciences, Bangalore, India, for recording spectral data.

 

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Received 26 October 2007
Revised 14 December 2007
Accepted 21 January 2008

 

 

* To whom correspondence should be addressed. E-mail: naga_raju04@yahoo.co.in