Synthesis and antibacterial activity of new 2-aryloxy-6-bromo-3-(4-chlorophenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine2-oxides

Gandavaram Syam Prasad,Pallam Reddy Haranath,Kachi Reddy Kishore Kumar Reddy,Boppudi Hari Babu,Cirandur Suresh Reddy

doi:10.3998/ark.5550190.0007.d17

Gandavaram Syam Prasad, Pallam Reddy Haranath + Show 3 more

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https://doi.org/10.3998/ark.5550190.0007.d17

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Abstract

Aryloxy-6-bromo-3-(4-chlorophenyl)-3,4-dihydro-benzo(e)(1,3,2)oxazaphosphinine 2-oxides 3 have been synthesized by the reaction of 4-bromo-2-((4-chlorophenylamino)methyl)phenol (1) with various aryl phosphorodichloridates 2a-i in the presence of triethylamine in dry toluene- tetrahydrofuran at 45-50 °C. Products 3 were characterized by IR, 1 H, 13 C, and 31 P NMR spectra, and their antibacterial activity was evaluated.

Highlights

Organophosphorus compounds being ubiquitous in nature have found multifaceted applications. 1,3,2-Oxazaphosphinine derivatives, cyclophosphamide and its analogues, isophosphamides are clinically useful anticancer drugs;1–2 organophosphorus esters are used as pesticides3 and insecticides.4a–b In view of this, a series of 2-aryloxy-6-bromo-3-(4-chlorophenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine 2-oxides 3 has been synthesized
The compounds were assayed for antibacterial activity against six registered bacterial isolates, which were obtained from the NCIM (National Collection of Industrial Microorganisms, National Chemical Laboratories, Pune-411 003, India): Two Gram positive bacterial isolates, Staphylococcus aureus (NCIM No 5021, ATCC No 25923), Bacillus subtilis (NCIM No 2063, ATCC No 6633) and four Gram negative bacteria, Escherichia coli (NCIM No: 2931, ATCC No 25922), Pseudomonas aeruginosa (NCIM No 5029, ATCC No 27853), Salmonella typhimurium (NCIM No 2501, ATCC No, 23564) and Klebsiella pneumoniae (NCIM No 2957)
The reactions were performed in dry toluenetetrahydrofuran in the presence of triethylamine, because all reactants are readily soluble in this solvent at room temperature, and products 3 do not decompose at the reaction temperature of 4550 °C

Summary

Introduction

Organophosphorus compounds being ubiquitous in nature have found multifaceted applications. 1,3,2-Oxazaphosphinine derivatives, cyclophosphamide and its analogues, isophosphamides are clinically useful anticancer drugs;1–2 organophosphorus esters are used as pesticides3 and insecticides.4a–b In view of this, a series of 2-aryloxy-6-bromo-3-(4-chlorophenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine 2-oxides 3 has been synthesized. The synthetic route involves preparation of 4-bromo-2-[(4-chlorophenylamino)methyl]phenol (1) (by condensation of 4-chloroaniline, 4-bromophenol and aqueous formaldehyde10) followed by the cyclocondensation of 1 with aryl phosphorodichloridates5 2a-i in the presence of triethylamine in toluene-tetrahydrofuran at 45–50 °C (Scheme 1). Product structures 3 were characterized by elemental analyses, IR, 1H, 13C, and 31P NMR spectra (Tables 1 and 2).

Results

Conclusion