A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids

Tetrahedron Letters

Volumn 51, Issue 48, 2010, Pages 6338-6341

  Nagendra, G ^a   Lamani, Ravi S ^a   Narendra, N ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Cyclization; Diacylhydrazine; Oxadiazole; Peptidomimetics; Thiadiazole

Indexed keywords

1 (3 DIMETHYLAMINOPROPYL) 3 ETHYLCARBODIIMIDE; 1,3,4 OXADIAZOLE DERIVATIVE; 1,3,4 THIADIAZOLE DERIVATIVE; AMINO ACID; DIACYLHYDRAZINE; HYDRAZINE DERIVATIVE; PEPTIDOMIMETIC AGENT; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLODEHYDRATION; DESULFURIZATION; DRUG SYNTHESIS;

EID: 78049362737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.122     Document Type: Article

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50. 2O]-Ala-Fmoc 5b, 5c were studied. The alanyl methyl groups were resonated as distinct doublets at δ 1.30 and 1.34 for 4b and at δ 1.28 and 1.32 for 4c, at δ 1.31 and 1.35 for 5b and at δ 1.28 and 1.32 for 5c supporting their enantiopurity.
51. The enantiopurity of each of the above compounds was further supported by the HPLC analysis by using column: Agilent Eclipse XDB-C18 (flow rate 0.5 mL/min; eluting with 0.1% TFA water-acetonitrile; 30-100% in 30 min). Diacylhydrazines 3b and 3c showed single peak with retention time at 12.48 and 12.06 min, respectively. Similarly in the case of 1,3,4-thiadiazole derivatives, single retention time at 9.55 min for 4b and at 9.43 min for 4c were observed, whereas the corresponding enantiopure 1,3,4-oxadiazoles 5b and 5c showed single retention times at 11.73, 11.67 min, respectively.