Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c][1,3,2]diazaphosphole-2-oxides

被引:13
作者
Babu, Y. Hari [1 ]
Kumar, M. Anil [1 ]
Srinivasulu, K. [1 ]
Reddy, C. Suresh [1 ]
Raju, C. Naga [1 ]
机构
[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
关键词
3,4-diamino-1,2,5-oxadiazole; 3,4-diaminofurazan; Kirsanov isocyanate; carboxamidophosphoryldichloride;
D O I
10.3998/ark.5550190.0007.f23
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some novel 2-(heterylcarboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c][1,3,2]diazaphosphole- 2-oxides (4-13) have been synthesized from reaction of 3,4-diamino-1,2,5-oxadiazole (3) with various dichlorophosphinylcarboxamides (2), which were prepared by C-acylation of electron-rich heterocyclic compounds with dichloro isocyanato phosphine oxide (Kirsanov isocyanate) (1) in dry octane, in the presence of triethylamine at 50-60 degrees C. Their structures were determined by IR, H-1, C-13, P-31 NMR and mass spectral ( MS) studies. They were screened for antifungal and antibacterial activity against Curvularia lunata / Aspergillus niger and Staphylococcus aureus / Escherichia coli, respectively. Most of these compounds exhibited moderate activity in the assays.
引用
收藏
页码:189 / 197
页数:9
相关论文
共 33 条
[1]  
ARDRIANANO VG, 1984, CHEM HETEROCYCL COMP, P937
[2]  
ARNOLD H, 1961, ARZNEIMITTEL-FORSCH, V11, P143
[3]   THE INFRA-RED SPECTRA OF SOME ORGANO-PHOSPHORUS ESTERS [J].
BELLAMY, LJ ;
BEECHER, L .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (FEB) :475-483
[4]   CHARACTERISTIC INFRA-RED ABSORPTION FREQUENCIES OF ORGANOPHOSPHORUS COMPOUNDS .6. BONDS BETWEEN PHOSPHORUS AND NITROGEN [J].
CHITTENDEN, RA ;
THOMAS, LC .
SPECTROCHIMICA ACTA, 1966, 22 (08) :1449-+
[5]  
COLLE JG, 1989, MACKIE MCCARTNEY PRA, V2
[6]  
Corbrjdge D.E.C., 1956, J APPL CHEM, V6, P456
[7]  
Daash L. W., 1961, ANAL CHEM, V23, P853
[8]   Lipoxygenase Metabolites of α-linolenic Acid in the Development of Resistance in Pigeonpea, Cajanus cajan (L.) Millsp, Seedlings Against Fusarium udum Infection [J].
P. Uma Maheswari Devi ;
P. Srinivas Reddy ;
N.R. Usha Rani ;
K.J. Reddy ;
M. Narsa Reddy ;
P. Reddanna .
European Journal of Plant Pathology, 2000, 106 (9) :857-865
[9]   POTENTIAL CARCINOLYTIC AGENTS RELATED TO CYCLOPHOSPHAMIDE [J].
FRIEDMAN, OM ;
TILL, HR ;
PAPANASTASSIOU, ZB ;
LEVI, RS ;
WHALEY, WM .
JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (01) :82-&
[10]  
Haranath P, 2004, HETEROCYCL COMMUN, V10, P457