195191-89-0

Basic information

• Product Name: Benzoic acid, 4-[(5-bromo-1-oxopentyl)amino]-, methyl ester
• CAS NO: 195191-89-0
• Molecular Formula: C13H16BrNO3
• Molecular Weight: 314.179
• Mol File: 195191-89-0.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-[(5-bromo-1-oxopentyl)amino]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-[(5-bromo-1-oxopentyl)amino]-, methyl ester(195191-89-0)
• EPA Substance Registry System: Benzoic acid, 4-[(5-bromo-1-oxopentyl)amino]-, methyl ester(195191-89-0)

Safety Data

• Hazardous Substances Data: 195191-89-0(Hazardous Substances Data)

Upstream product

• 2067-33-6 5-bromopentanoic acid 
• 619-45-4 4-methoxycarbonyl aniline 
• 4509-90-4 5-bromovaleroyl chloride 

Downstream Products

• 195191-92-5 4-[5-(Acridin-9-ylamino)-pentanoylamino]-benzoic acid 
• 195191-91-4 4-(5-azido-pentanoylamino)-benzoic acid 
• 64124-33-0 4-(5-Aminovalerylamino)benzoesaeure 
• 195191-90-3 4-(5-Azido-pentanoylamino)-benzoic acid methyl ester 

Relevant articles and documents

Synthesis and SAR studies of analogues of 4-(3,3-dimethyl-butyrylamino)-3,5-difluoro-N-thiazol-2-yl-benzamide (Lu AA41063) as adenosine A2A receptor ligands with improved aqueous solubility

An adenosine A2A receptor antagonist may be useful for the treatment of Parkinson's disease. Synthesis and structure-activity studies starting from 4-(3,3-dimethylbutyrylamino)-3,5-difluoro-N-thiazol-2-yl-benzamide (Lu AA41063, 4) led to a novel series of human (h) A2A receptor antagonists with improved aqueous solubility. Compound 22 was identified as a key representative from the series, displaying submicromolar hA2A receptor affinity and excellent aqueous solubility. Compound 22 also displayed good in vitro pharmacokinetic properties and is considered a good starting point for further lead optimisation toward hA2A receptor antagonists with improved druggability properties.

Design, synthesis, and evaluation of N-aroyloxy-2-thiopyridones as DNA photocleaving reagents

N-Benzoyloxy-2-thiopyridone (12) was shown to induce single-strand nicks in duplex DNA upon irradiation with visible light (λ~350nm). This finding led to the design of a series of compounds, in which an acridinyl nucleus was covalently linked to the N-benzoyloxy-2-thiopyridone unit. These conjugates (15, 16, 17 and 18) were synthesized and evaluated as novel DNA photocleaving reagents. Optimal photocleaving activity was observed for conjugate 16, in which a flexible polymethylene spacer of 4 carbons was used to connect the aminoacridine entity to the thiopyridone. This compound was shown to cleave DNA at low μM concentrations and was approximately two-orders of magnitude more efficient than the parent N-benzoyloxy-2-thiopyridone (12). Furthermore, the DNA cleavage ladders induced by 16 and 12 were found to be identical and of no significant sequence selectivity. These data suggest that the N-aroyloxy-2-thiopyridones can be used for the design of new DNA photocleaving reagents with potential use as 'photofootprinting agents' or as 'site-directed photonucleases'. Copyright (C) 1999 Elsevier Science Ltd.

Photochemical cleavage of duplex DNA by N-benzoyloxy-2-thiopyridone linked to 9-aminoacridine

Upon illumination N-aroyloxy-2-thiopyridones induce non-specific single-strand nicks in duplex DNA at micromolar concentrations.