103261-01-4

Basic information

• Product Name: 7-Benzofurancarbonylchloride,2,3-dihydro-2-methyl-(6CI)
• Synonyms: 7-Benzofurancarbonylchloride,2,3-dihydro-2-methyl-(6CI)
• CAS NO: 103261-01-4
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.63026
• Product Categories: ACIDHALIDE
• Mol File: 103261-01-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Benzofurancarbonylchloride,2,3-dihydro-2-methyl-(6CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Benzofurancarbonylchloride,2,3-dihydro-2-methyl-(6CI)(103261-01-4)
• EPA Substance Registry System: 7-Benzofurancarbonylchloride,2,3-dihydro-2-methyl-(6CI)(103261-01-4)

Safety Data

• Hazardous Substances Data: 103261-01-4(Hazardous Substances Data)

Upstream product

• 6282-42-4 methyl 2-allyloxybenzoate 
• 69-72-7 salicylic acid 
• 119-36-8 methyl salicylate 
• 41176-57-2 2,3-dihydro-2-methyl-7-benzofurancarbonsaeuremethylester 
• 31456-98-1 methyl 3-allyl-salicylate 
• 1745-81-9 o-Allylphenol 
• 31457-03-1 2-methyl-2,3-dihydrobenzo[b]furan-7-carboxylic acid 
• 1746-11-8 2-methyl-2,3-dihydro-1-benzofuran 

Downstream Products

• 31457-07-5 2-methyl-7-benzofurancarbonsaeure 
• 149530-57-4 2,3-Dihydro-N-<4-(1,1-dimethylethyl)phenylmethyl>-N,2-dimethyl-7-benzofurancarboxamid 

Relevant articles and documents

Synthesis and vasorelaxant potency of monagra. A chiral 5-(2-methyl-2,3-dihydro-7-benzofuryl)-pyrazolopyrimidone analog of viagra

Synthesis and properties of a chiral 5-(2-methyl-2,3-dihydro-7-benzofuryl)pyrazolo[4,3-d]pyrimidin-7-one (3), an analog of Viagra (1) and Biagra (2), are described. The key material, (±)-3-methyl-2,3-dihydrobenzofuran-7-carboxylic acid (8a) was resolved into the (S)-8b (95% ee) and (R)-8c (99% ee) enantiomers using, respectively, (-)-cinchonidine and (+)-cinchonine. The absolute configuration of 8c was determined as R by X-Ray measurements. Preliminary in vitro experiments on rat isolated thoracic aorta show that the vasorelaxant potency of 3b,c is truly higher than that of 1 and 2.

Zatosetron, a Potent, Selective, and Long-Acting 5HT3 Receptor Antagonist: Synthesis and Structure-Activity Relationships

Antagonists of 5HT3 receptors are clinically effective in treating nausea and emesis associated with certain oncolytic drugs, including cisplatin.Moreover, these agents may be useful in pharmacological management of several central nervous system disorders, including anxiety, schizophrenia, dementia, and substance abuse.Our studies on aroyltropanamides led to the discovery that dihydrobenzofuranyl esters and amides are potent 5HT3 receptor antagonists.Simple benzoyl derivatives of tropine and 3α-aminotropane possessed weak 5HT3 receptor antagonist activity, as judged by blockade of bradycardia produced by iv injection of serotonin (5HT) to anesthetized rats.Within this series, use of benzofuran-7-carboxamide as the aroyl moiety led to a substantial increase of 5HT3 receptor affinity.The optimal 5HT3 receptor antagonist identified via extensive SAR studies was endo-5-chloro-2,3-dihydro-2,2-dimethyl-N-(8-methyl-8-azabicyclooct-3-yl)-7-benzofurancarboxamide (Z)-2-butenedioate (zatosetron maleate).The 7-carbamyl regiochemistry, dimethyl substitution, chloro substituent, and endo stereochemistry were all crucial elements of the SAR.Zatosetron maleate was a potent antagonist of 5HT-induced bradycardia in rats (ED50=0.86 μg/kg iv).Low oral doses of zatosetron (30 μg/kg) produced long-lasting antagonism of 5HT3 receptors, as evidenced by blockade of 5HT-induced bradycardia for longer than 6 h in rats.Moreover, this compound did not produce hemodynamic effects after iv administration to rats, nor did it block carbamylcholine-induced bradycardia in doses that markedly blocked 5HT3 receptors.Thus, zatosetron is a potent, selective, orally effective 5HT3 receptor antagonist with a long duration of action in rats.