54035-70-0

Upstream product

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

Downstream Products

• 100313-34-6 1-benzyl-3-(ethoxycarbonyl)-carbodiimide 
• 263390-02-9 C₂H₅O₂CNC(NHCH₂C₆H₅)NHC₄H₉ 
• 263390-01-8 N,N-dibenzyl-guanidine carbamic acid ethyl ester 
• 426836-93-3 C₁₉H₂₃N₃O₂ 
• 426836-87-5 C₁₈H₂₀N₄O₄ 
• 426836-91-1 C₂₀H₂₅N₃O₄ 
• 426836-86-4 C₁₈H₂₂N₄O₂ 
• 426836-96-6 C₁₄H₂₁N₃O₂ 
• 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 
• 1581260-99-2 C₁₃H₁₇N₃O₄ 
• 1424635-83-5 (Z)-N-(3-benzylthiazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide 

Relevant academic research and scientific papers

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.

PYRROLO [2,3-B]PYRIDINE-3-CARBOXAMIDE COMPOSITIONS AND METHODS FOR AMELIORATING HEARING LOSS

N-(3-Substituted thiazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamides and N-(3-substituted oxazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamides (I) and (II) are disclosed. The compounds activate Yap and inhibit Lats kinases. They are therefore useful for treating hearing loss.

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 highly efficient method for the synthesis of guanidinium derivatives

A high yielding synthesis of guanidiniums with the use of the ethyl carbamate protecting group is presented. This strategy eliminates many steric hindrance and electronic problems. The deprotection of the products by Me3SiBr is also demonstrated.

A New and Efficient Synthesis of Guanosine

New methodology for the preparation of guanosine-type nucleoside analogues from o-amino carbamyl nucleoside precursors has been developed and is demonstrated by the three-step, high-yield synthesis of guanosine (16) from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (1, AICA-riboside).Treatment of 1-(alkoxycarbonyl)-3-(arylmethyl)thioureas 8 with phosgene in the presence of triethylamine affords the highly electrophilic 1-(alkoxycarbonyl)-3-(arylmethyl)carbodiimide reagents 9 in high yield.These reagents are shown to condense with AICA-riboside readily at room temperature to afford N-acyl-N'-(arylmethyl)guanidino-substituted imidazole nucleoside derivatives.One of these derivatives, 5-(N-benzyl-N'-(ethoxycarbonyl)guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (11a), is smoothly debenzylated with cyclohexene in the presence of Pd(0) to afford 5-(N-(ethoxycarbonyl)guanidino)-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (14).Prolonged heating of 14 in ethanol at reflux affords N-2-(ethoxycarbonyl)guanosine (15) in high yield.The ethoxycarbonyl protecting group of 15 is removed with concentrated NH4OH/pyridine to afford guanosine.This new methodology is much more efficient than those previously reported and should find application for the preparation of a wide variety of guanosine-type nucleoside analogues.