14538-17-1

Basic information

• Product Name: N-(5-nitro-1,3-thiazol-2-yl)pentanamide
• Synonyms: pentanamide, N-(5-nitro-2-thiazolyl)-
• CAS NO: 14538-17-1
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.2562
• Mol File: 14538-17-1.mol
• Article Data: 3

Chemical Properties

• Density: 1.376g/cm³
• Refractive Index: 1.605
• CAS DataBase Reference: N-(5-nitro-1,3-thiazol-2-yl)pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-nitro-1,3-thiazol-2-yl)pentanamide(14538-17-1)
• EPA Substance Registry System: N-(5-nitro-1,3-thiazol-2-yl)pentanamide(14538-17-1)

Safety Data

• Hazardous Substances Data: 14538-17-1(Hazardous Substances Data)

Upstream product

• 69212-60-8 pentanoic acid thiazol-2-ylamide 
• 121-66-4 2-amino-5-nitro-1,3-thiazole 
• 638-29-9 n-valeryl chloride 
• 109-52-4 valeric acid 

Relevant articles and documents

2-Acylamino-5-nitro-1,3-thiazoles: Preparation and in vitro bioevaluation against four neglected protozoan parasites

The 2-acylamino-5-nitro-1,3-thiazole derivatives (1-14) were prepared using a one step reaction. All compounds were tested in vitro against four neglected protozoan parasites (Giardia intestinalis, Trichomonas vaginalis, Leishmania amazonensis and Trypanosoma cruzi). Acetamide (9), valeroylamide (10), benzamide (12), methylcarbamate (13) and ethyloxamate (14) derivatives were the most active compounds against G. intestinalis and T. vaginalis, showing nanomolar inhibition. Compound 13 (IC50 = 10 nM), was 536-times more active than metronidazole, and 121-fold more effective than nitazoxanide against G. intestinalis. Compound 14 was 29-times more active than metronidazole and 6.5-fold more potent than nitazoxanide against T. vaginalis. Ureic derivatives 2, 3 and 5 showed moderate activity against L. amazonensis. None of them were active against T. cruzi. Ligand efficiency indexes analysis revealed higher intrinsic quality of the most active 2-acylamino derivatives than nitazoxanide and metronidazole. In silico toxicity profile was also computed for the most active compounds. A very low in vitro mammalian cytotoxicity was obtained for 13 and 14, showing selectivity indexes (SI) of 246,300 and 141,500, respectively. Nitazoxanide showed an excellent leishmanicidal and trypanocidal effect, repurposing this drug as potential new antikinetoplastid parasite compound.

SYNTHESIS OF NITAZOLE AND ITS ANALOGS

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