304018-04-0

Basic information

• Product Name: (2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHEN-3-YL)-(4-CHLORO-PHENYL)-METHANONE
• Synonyms: (2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIEN-3-YL)(4-CHLOROPHENYL)METHANONE;(2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHEN-3-YL)-(4-CHLORO-PHENYL)-METHANONE
• CAS NO: 304018-04-0
• Molecular Formula: C14H12ClNOS
• Molecular Weight: 277.77
• Mol File: 304018-04-0.mol

Chemical Properties

• Boiling Point: 520°C at 760 mmHg
• Flash Point: 268.3°C
• Appearance: /
• Density: 1.386g/cm³
• Vapor Pressure: 6.5E-11mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: (2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHEN-3-YL)-(4-CHLORO-PHENYL)-METHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHEN-3-YL)-(4-CHLORO-PHENYL)-METHANONE(304018-04-0)
• EPA Substance Registry System: (2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHEN-3-YL)-(4-CHLORO-PHENYL)-METHANONE(304018-04-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 304018-04-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12ClNOS/c15-9-6-4-8(5-7-9)13(17)12-10-2-1-3-11(10)18-14(12)16/h4-7H,1-3,16H2

Upstream product

• 536-38-9 4-chlorobenzoylmethyl bromide 
• 120-92-3 cyclopentanone 
• 4640-66-8 p-chlorobenzoylacetonitrile 

Relevant articles and documents

Microwave-assisted synthesis of 2-aminothiophene derivatives via improved gewald reactions

In this paper, a new and efficient method was developed to prepare 2-aminothiophene derivatives through improved Gewald reaction. Thirty-one final products were synthesized under microwave radiation for 30 min with 57%-95% isolated yields. All the product

THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS

The present invention relates to a series of compounds of formula (A) having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

2-Amino-3-aroyl-4,5-alkylthiophenes: Agonist allosteric enhancers at human a1 adenosine receptors

2-Amino-3-benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor. The present report describes syntheses and assays of the AE activity at the human A1AR (hA1AR) of a panel of compounds consisting of nine 2-amino-3-aroylthiophenes (3a-i), eight 2-amino-3-benzoyl-4,5-dimethylthiophenes (12a-h), three 3-aroyl-2-carboxy-4,5-dimethylthiophenes (15a-c), 10 2-amino-3-benzoyl-5,6-dihydro-4H-cyclopenta[b]thiophenes (17a-j), 14 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophenes (18a-n), and 15 2-amino-3-benzoyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophenes (19a-o). An in vitro assay employing the A1AR agonist [125I]ABA and membranes from CHO-K1 cells stably expressing the hA1AR measured, as an index of AE activity, the ability of a candidate AE to stabilize the agonist-A1AR-G protein ternary complex. Compounds 3a-i had little or no AE activity, and compounds 12a-h had only modest activity, evidence that AE activity depended absolutely on the presence of at least a methyl group at C-4 and C-5. Compounds 17a-c lacked AE activity, suggesting the 2-amino group is essential. Polymethylene bridges linked thiophene C-4 and C-5 of compounds 17a-j, 18a-n, and 19a-o. AE activity increased with the size of the -(CH2)n- bridge, n = 3 1AR contains an allosteric binding site able to accommodate 3-aroyl substituents that are bulky and/or hydrophobic but not necessarily planar. A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5.

Synthesis and biological effects of a new series of 2-amino-3-benzoylthiophenes as allosteric enhancers of A1-adenosine receptor

New derivatives of PD 81,723, an allosteric enhancer of agonist binding to the A1-adenosine receptor, have been synthesized and evaluated in an intact cell assay. Compounds 3a, 3o and 3p appeared to be more potent than PD 81,723 and at a concentration of 0.1 μM caused significant reductions of cAMP content of CHO cells expressing the human A1-adenosine receptor. Compounds 4e and 4o appeared to be allosteric enhancers at a low concentration and antagonists at a higher concentration, whereas compounds 3c, 3g, 3s and 4l appeared to be weak antagonists that are also allosteric enhancers at the higher concentration of 10 μM. (C) 2000 Elsevier Science Ltd.