Synthesis of Optically Active 2-Amino-1,3,4-oxadiazoles and their Hybrid Peptides

被引：4
作者：
Madhu, Chilakapati [1 ]
Prabhu, Girish [1 ]
Pal, Rumpa [2 ]
Row, T. N. Guru [2 ]
Sureshbabu, Vommina V. [1 ]
机构：
[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560001, Karnataka, India
[2] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, Karnataka, India
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2015年 / 52卷 / 05期
关键词：
CONVENIENT SYNTHESIS; BUILDING-BLOCKS; AMINO-ACIDS; UGI-MCR; PEPTIDOMIMETICS; DESIGN; OXADIAZOLES; ANALOGS; RING;
D O I：
10.1002/jhet.2166
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthesis of 2-amino-1,3,4-oxadiazole derivatives of N-Cbz(benzyloxycarbonyl)/Boc-protected amino/peptide acids under sonication is described. The conditions involved in the present protocol are simple, mild, and racemization free. The utility of 2-amino group in the substituted oxadiazoles for the incorporation of peptide and ureido bonds to obtain hybrid peptidomimetics is also delineated. The 2-amino-1,3,4-oxadiazole 3b was obtained as a single crystal, and its molecular structure has been confirmed through X-ray crystallographic study.
引用
收藏
页码：1438 / 1446
页数：9
相关论文
共 50 条
[21]   Synthesis and anticancer evaluation of new lipophilic 1,2,4 and 1,3,4-oxadiazoles [J].
Caneschi, Wiliam ;
Enes, Karine Braga ;
de Mendonca, Camille Carvalho ;
Fernandes, Fabio de Souza ;
Miguel, Fabio Balbino ;
Martins, Jefferson da Silva ;
Le Hyaric, Mireille ;
Pinho, Roberto Rosas ;
Duarte, Lucas Mattos ;
Leal de Oliveira, Marcone Augusto ;
Dos Santos, Hello F. ;
Paz Lopes, Miriam Teresa ;
Dittz, Dalton ;
Silva, Heveline ;
Costa Couri, Mara Rubia .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 165 :18-30
[22]   Copper-catalyzed direct cross coupling of 1,3,4-oxadiazoles with trans-β-halostyrenes: synthesis of 2-E-vinyl 1,3,4-oxadiazoles [J].
Das, Biswanath ;
Reddy, Gandolla Chinna ;
Balasubramanyam, Penagaluri ;
Salvanna, N. .
TETRAHEDRON, 2012, 68 (01) :300-305
[23]   Electrophilically activated nitroalkanes in the synthesis of substituted 1,3,4-oxadiazoles from amino acid derivatives [J].
Alexander V. Aksenov ;
Nikita K. Kirilov ;
Nicolai A. Aksenov ;
Nikolai A. Arutiunov ;
Dmitrii A. Aksenov ;
Michael Rubin .
Chemistry of Heterocyclic Compounds, 2022, 58 :32-36
[24]   Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles [J].
Aksenov, Alexander V. ;
Khamraev, Vladislav ;
Aksenov, Nicolai A. ;
Kirilov, Nikita K. ;
Domenyuk, Dmitriy A. ;
Zelensky, Vladimir A. ;
Rubin, Michael .
RSC ADVANCES, 2019, 9 (12) :6636-6642
[25]   Synthesis and biological property of some novel 1,3,4-oxadiazoles [J].
Ramaprasad, G. C. ;
Kalluraya, Balakrishna ;
Kumar, B. Sunil ;
Hunnur, Ravindra K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) :4587-4593
[26]   Novel pyrazole integrated 1,3,4-oxadiazoles: Synthesis, characterization and antimicrobial evaluation [J].
Ningaiah, Srikantamurthy ;
Bhadraiah, Umesha K. ;
Doddaramappa, Shridevi D. ;
Keshavamurthy, Shubakara ;
Javarasetty, Chethan .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (01) :245-248
[27]   Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl [J].
Gnanasekaran, Krishna Kumar ;
Nammalwar, Baskar ;
Murie, Maeghan ;
Bunce, Richard A. .
TETRAHEDRON LETTERS, 2014, 55 (50) :6776-6778
[28]   Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles [J].
Padmavathi, V. ;
Reddy, S. Nagi ;
Reddy, G. Dinneswara ;
Padmaja, A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :4246-4251
[29]   A Novel One-Pot Synthesis of 2-Alkylthio-1,3,4-oxadiazoles in Water [J].
Aryanasab, F. ;
Maleki, H. ;
Saidi, M. R. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (02) :525-530
[30]   Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles [J].
Desai, N. C. ;
Bhatt, Nayan ;
Somani, Hardik ;
Trivedi, Amit .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 :54-59
12345