Synthesis and antimicrobial activity of 1-[(substituted carbamoyl)amino]-1H,3H-1λ5-[1,3,2]oxazaphospholo[3,4-a] benzimidazol-1-ones

被引:2
|
作者
Anasuyamma, U.
Haranath, P.
Kumar, M. Anil
Reddy, C. Suresh [1 ]
Raju, C. Naga
机构
[1] Sri Venkateswara Univ, Coll Engn, Dept Chem, Tirupati 517502, Andhra Pradesh, India
[2] Univ Murcia, Dept Organ Chem, Murcia, Spain
关键词
carbamido phosphoric acid dichloride; isocyanatophosphonic dichloride; oxazaphosphospholo benzimidazols;
D O I
10.1080/00397910701483886
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-[(Substituted carbamoyl)amino]-1H,3H-1 lambda(5) -[1,3,2]oxazaphospholo[3,4-a] benzimidazol-l-ones were synthesized by reacting benzimidazole 2-methanol (4) with different chlorides of carbamidophosphoric acids (3) in the presence of triethylamine at 40-45 degrees C. Their H-1, C-13, and P-31 NMR spectral data were discussed. The title compounds were tested for their activity against the fungi Aspergillus niger and Fusarium solani and bacteria Staphylococcus aureus and Escherichia coli. These compounds showed moderate antibacterial activity when compared with antifungal activity.
引用
收藏
页码:3429 / 3437
页数:9
相关论文
共 50 条
  • [1] Synthesis and antimicrobial activity of novel (3a,S)-1-(aminoacid ester)-3a,4-dihydro-3H-1λ5-[1,3,2] oxazaphospholo[3,4-a] indol-1-oxides
    Sankar, A. Uma Ravi
    Kumar, B. Siva
    Reddy, M. Veera Narayana
    Haribabu, B.
    Raju, C. Naga
    ARKIVOC, 2007, : 300 - 308
  • [2] Synthesis of novel (3a,S)-1-aryl/aryloxy/alkoxy-3a,4-dihydro-3H-1λ5-[1,3,2]oxazaphospholo [3,4-a] indole-1-ones, thiones, and selenones
    Babu, B. Hari
    Prasad, G. Syam
    Raju, C. Naga
    Reddy, C. Suresh
    SYNTHETIC COMMUNICATIONS, 2008, 38 (09) : 1398 - 1406
  • [3] SYNTHESIS OF SUBSTITUTED 3-HYDROXY-1H,5H-PYRIDO[1,2-A]-BENZIMIDAZOL-1-ONES AS POSSIBLE ANTIMICROBIAL AND ANTINEOPLASTIC AGENTS
    SOLIMAN, FSG
    RIDA, SM
    BADAWY, ESAM
    KAPPE, T
    ARCHIV DER PHARMAZIE, 1984, 317 (11) : 951 - 958
  • [4] 1-(2-Fluorophenyl)- and 1-(3-fluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole
    Bruno, G
    Grasso, S
    Monforte, P
    Nicolo, F
    Scopelliti, R
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 764 - 767
  • [5] New substituted 2-aminomethyl-2-oxo-2λ5-perhydro-[1,3,2]oxazaphospholo [3,4-a]pyridine: Design, synthesis and antimicrobial activity
    Golla, Madhava
    Devineni, Subba Rao
    Syed, Rasheed
    Rayalacheru, Bhanu Kiran
    Maram, Rajasekhar
    Raju, Chamarthi Naga
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (07) : 794 - 798
  • [6] 3-(α-Chlorobenzyl)quinoxalin-2(1H)-ones as Versatile Reagents for the Synthesis of 3-Benzylquinoxalin-2(1H)-ones and Thiazolo[3,4-a]quinoxalin-4(5H)-ones
    Mamedov, Vakhid A.
    Zhukova, Nataliya A.
    Syakaev, Victor V.
    Beschastnova, Tat'yana N.
    Kadyrova, Milyausha S.
    Isaeva, Anastasiya O.
    Mamedova, Sevil, V
    Gavrilova, Elena L.
    Latypov, Shamil K.
    Sinyashin, Oleg G.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (08) : 2221 - 2234
  • [7] 1-[3,5-bis(trifluoromethyl)phenyl]-1H,3H-thiazolo[3,4-a]benzimidazole
    Bruno, G
    Monforte, AM
    Nicolo, F
    Scopelliti, R
    Zappala, M
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 2533 - 2535
  • [8] Synthesis and antitumour activity of 1H,3H-thiazolo[3,4-a]benzimidazole derivatives
    Chimirri, A
    Monforte, P
    Musumeci, L
    Rao, A
    Zappalà, M
    Monforte, AM
    ARCHIV DER PHARMAZIE, 2001, 334 (06) : 203 - 208
  • [9] New Strategy of the Synthesis of 3,4-Dihydropyrimido[1,2-a]benzimidazol-2(1H)-ones
    Kharaneko, A. O.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (09) : 1363 - 1368
  • [10] New Strategy of the Synthesis of 3,4-Dihydropyrimido[1,2-a]benzimidazol-2(1H)-ones
    A. O. Kharaneko
    Russian Journal of Organic Chemistry, 2018, 54 : 1363 - 1368