54035-70-0

Basic information

• Product Name: Carbamic acid, [[(phenylmethyl)amino]thioxomethyl]-, ethyl ester
• Synonyms: N-benzyl-N'-ethoxycarbonylthiourea;1-benzyl-3-(ethoxycarbonyl)thiourea;ethoxy-N-{[benzylamino]thioxomethyl}carboxamide;N-Benzyl-thioharnstoff-N'-carbonsaeureaethylester;a-Benzyl-monothioallophansaeure-aethylester;Carbamic acid,[[(phenylmethyl)amino]thioxomethyl]-,ethyl ester;4-benzyl-3-thio-allophanic acid ethyl ester;N-ethoxycarbonyl-N'-benzyl-thiourea;4-Benzyl-3-thio-allophansaeure-aethylester
• CAS NO: 54035-70-0
• Molecular Formula: C11H14N2O2S
• Molecular Weight: 238.31
• Mol File: 54035-70-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [[(phenylmethyl)amino]thioxomethyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [[(phenylmethyl)amino]thioxomethyl]-, ethyl ester(54035-70-0)
• EPA Substance Registry System: Carbamic acid, [[(phenylmethyl)amino]thioxomethyl]-, ethyl ester(54035-70-0)

Safety Data

• Hazardous Substances Data: 54035-70-0(Hazardous Substances Data)

Upstream product

• 16182-04-0 Ethoxycarbonyl isothiocyanate 
• 100-46-9 benzylamine 

Downstream Products

• 426836-93-3 C₁₉H₂₃N₃O₂ 
• 426836-87-5 C₁₈H₂₀N₄O₄ 
• 426836-91-1 C₂₀H₂₅N₃O₄ 
• 426836-86-4 C₁₈H₂₂N₄O₂ 
• 100313-39-1 5-(3-benzyl-3'-(ethoxycarbonyl)-1-guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 1318804-79-3 N-Benzyl-N'-ethoxycarbonyl-N''-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranos-1-yl)oxy]-L-guanidine 
• 1318804-84-0 N-benzyl-N'-ethoxycarbonyl-N''-[(tetrahydro-2H-pyran-1-yl)oxy]guanidine 
• 1318804-80-6 N-benzyl-N'-ethoxycarbonyl-N''-[(β-D-galactopyranos-1-yl)oxy]-L-guanidine 
• 1318804-86-2 C₁₁H₁₅N₃O₃ 
• 1424635-83-5 (Z)-N-(3-benzylthiazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide 
• 1581260-99-2 C₁₃H₁₇N₃O₄ 

Relevant articles and documents

Prodrug design for the potent cardiovascular agent Nω- hydroxy-l-arginine (NOHA): Synthetic approaches and physicochemical characterization

Nω-Hydroxy-l-arginine (NOHA) - the physiological nitric oxide precursor - is the intermediate of NO synthase (NOS) catalysis. Besides the important fact of releasing NO mainly at the NOS-side of action, NOHA also represents a potent inhibitor of arginases, making it an ideal therapeutic tool to treat cardiovascular diseases that are associated with endothelial dysfunction. Here, we describe an approach to impart NOHA drug-like properties, particularly by wrapping up the chemically and metabolically instable N-hydroxyguanidine moiety with different prodrug groups. We present synthetic routes that deliver several more or less highly substituted NOHA derivatives in excellent yields. Versatile prodrug strategies were realized, including novel concepts of bioactivation. Prodrug candidates were primarily investigated regarding their hydrolytic and oxidative stabilities. Within the scope of this work, we essentially present the first prodrug approaches for an interesting pharmacophoric moiety, i.e., N-hydroxyguanidine. The Royal Society of Chemistry 2011.

Synthesis of 2-Amino-5-Carboxamide Thiazole Derivatives via Dehydrative Cyclization of Thiourea Intermediate Resin on Solid Phase

In this study, we synthesized 2-amino-5-carboxamide thiazole derivatives on solid phase. The synthesis of the library starts with the reductive amination of the 4-formyl-3-methoxy phenoxy resin to prevent isomer formation. The dehydrative cyclization of thiourea intermediate resin, which is the key step in the synthetic process, was successfully synthesized using α-bromoketone in the presence of the DMF so as to afford 2-amino-5-carboxylate thiazole resin. The resulting resin is coupled with various amines. Finally, the 2-amino-5-carboxamide thiazole resin was cleaved from the polymer support using a TFA and DCM cocktail. The physicochemical properties of the proposed 2-amino-5-carboxamide thiazole derivatives were calculated and showed potential to be an reasonable oral bioavailability drug properties as determined by Lipinski's Rule.

A versatile one-pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates

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