37653-67-1

Basic information

• Product Name: Carbamic acid, [4-(chlorocarbonyl)phenyl]-, phenylmethyl ester
• Synonyms: p-benzyloxycarbonylaminobenzoyl chloride;Carbamic acid,[4-(chlorocarbonyl)phenyl]-,phenylmethyl ester;p-N-benzyloxycarbonylaminobenzoyl chloride;N-benzyloxycarbonyl-4-aminobenzoyl chloride;4-[(benzyloxycarbonyl)amino]benzoyl chloride
• CAS NO: 37653-67-1
• Molecular Formula: C15H12ClNO3
• Molecular Weight: 289.718
• Mol File: 37653-67-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [4-(chlorocarbonyl)phenyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [4-(chlorocarbonyl)phenyl]-, phenylmethyl ester(37653-67-1)
• EPA Substance Registry System: Carbamic acid, [4-(chlorocarbonyl)phenyl]-, phenylmethyl ester(37653-67-1)

Safety Data

• Hazardous Substances Data: 37653-67-1(Hazardous Substances Data)

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 501-53-1 benzyl chloroformate 
• 5330-71-2 4-(((benzyloxy)carbonyl)amino)benzoic acid 

Downstream Products

• 117559-38-3 tri-tert-butyl N-benzoyl>-L-γ-glutamyl>-L-glutamate 
• 117559-39-4 tetra-tert-butyl N-benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 
• 117559-40-7 penta-tert-butyl N-benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 
• 117559-41-8 hexa-tert-butyl N-benzoyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-γ-glutamyl>-L-glutamate 
• 120122-23-8 methyl p-benzyloxycarbonylaminobenzoyl-(γ-t-butyloxy)glutamyl-γ-aminobutyrate 
• 80590-76-7 5-carbamoyl-1H-imidazole-4-yl p-N-benzyloxycarbonylaminobenzoate 
• 54-62-6 aminopterin 
• 247592-37-6 p-tritylphenyl 4-aminobenzoate 
• 258861-98-2 C₃₉H₃₁N₃O₂ 
• 247592-36-5 (4-aminobenz)-p-tritylanilide 

Relevant articles and documents

Total Synthesis of Nucleoside Antibiotics Amicetin, Plicacetin, and Cytosaminomycin A—D

Amicetin and congeners constitute a small family of complex pyrimidine nucleosides, which exhibit strong antibiotic activities against Gram-positive bacteria and notably against strains of Mycobacterium tuberculosis. Herein, we report chemical synthesis of a series of disaccharide congeners of the amicetin family, including amicetin, plicacetin, and cytosaminomycin A—D. It is the first time for successful synthesis of amicetin, the prototypical member, and cytosaminomycins. The synthetic approach employs glycosyl N-phenyltrifluoroacetimidate and thioglycoside donors to construct the characteristic aminodeoxydisaccharides consisting of α-(1→4)-glycosidic linkage, uses gold(I)-catalyzed N-glycosylation to furnish 2-deoxy-β-nucleosides, and finally exploits amidation and global deprotection to complete the syntheses. It is noteworthy that the 3-O-protecting group in the 2-deoxydisaccharide donors is found to be crucial for a successful N-glycosylation to assemble the cytosaminomycin disaccharide nucleosides.

Synthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis

A series of novel hydrogen peroxide sensitive prodrugs of methotrexate (MTX) and aminopterin (AMT) were synthesized and evaluated for therapeutic efficacy in mice with collagen induced arthritis (CIA) as a model of chronic rheumatoid arthritis (RA). The prodrug strategy selected is based on ROS-labile 4-methylphenylboronic acid promoieties linked to the drugs via a carbamate linkage or a direct C-N bond. Activation under pathophysiological concentrations of H2O2 proved to be effective, and prodrug candidates were selected in agreement with relevant in vitro physicochemical and pharmacokinetic assays. Selected candidates showed moderate to good solubility, high chemical and enzymatic stability, and therapeutic efficacy comparable to the parent drugs in the CIA model. Importantly, the prodrugs displayed the expected safer toxicity profile and increased therapeutic window compared to MTX and AMT while maintaining a comparable therapeutic efficacy, which is highly encouraging for future use in RA patients.