123040-50-6

Basic information

• Product Name: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE
• Synonyms: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE
• CAS NO: 123040-50-6
• Molecular Formula: C₁₀H₇Cl₂NO₃
• Molecular Weight: 260.07348
• Mol File: 123040-50-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(123040-50-6)
• EPA Substance Registry System: 6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE(123040-50-6)

Safety Data

• Hazardous Substances Data: 123040-50-6(Hazardous Substances Data)

Usage

Chemical compound

6-CHLORO-3,4-DIHYROGEN-4-METHYL-3-OXO-2H-1,4-BENZOXAZOLE-8-ACYLCHLORIDE

Classification

benzoxazoles

Substitutions

6-chloro on the benzene ring, acyl chloride functional group at the 8-position

Reactivity

highly reactive

Uses

intermediates in organic synthesis, formation of amides, esters, pharmaceuticals, agrochemicals, fine chemicals

Upstream product

• 123040-79-9 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid 
• 4068-78-4 methyl 5-chloro-2-hydroxybenzoate 
• 123040-75-5 methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate 
• 141761-83-3 6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid methyl ester 
• 5043-81-2 3-amino-5-chloro-2-hydroxybenzoic acid methyl ester 
• 5043-79-8 5-chloro-2-hydroxy-3-nitrobenzoic acid methyl ester 

Downstream Products

• 123040-69-7 azasetron 
• 123040-16-4 Azasetron hydrochloride 

Relevant articles and documents

Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides

Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).

Synthesis and pharmacology of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives, a new class of potent serotonin-3 (5-HT3) receptor antagonists

A series of 3,4-dihydro-3-oxo-1,4-benzoxazine-8-carboxamide derivatives was synthesized and evaluated for serotonin-3 (5-HT3) receptor antagonistic activity assessed by their ability to antagonize the von Bezold-Jarish (BJ) effect in rats. Derivatives bearing 1-azabicyclo[2.2.2]oct-3-yl moiety as a basic function attached to the carboxamide at position 8 showed more potent antagonistic activity than those bearing the other three basic moieties. Structure activity relationships of this series showed that methyl and chloro groups were more effective as substituents at positions 4 and 6, respectively. The representative compound 15 (Y-25130) in this series showed potent antagonistic activity on the BJ effect (ED50 = 1.3 μg/kg i.v.), high affinity for 5-HT3 receptor (K(i) = 2.9 nM) and complete protection against cisplatin-induced emesis in dogs at a dose of 0.1 mg/kg i.v.