174072-26-5

Basic information

• Product Name: 2-(4-Amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-7H-thieno[2,3-b]pyridin-4-one
• Synonyms: 2-(4-Amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-7H-thieno[2,3-b]pyridin-4-one;2-(4-Aminophenyl)-3-[[benzyl(methyl)amino]methyl]-7-[(2,6-difluorophenyl)methyl]-5-(2-methylpropanoyl)thieno[2,3-b]pyridin-4-one
• CAS NO: 174072-26-5
• Molecular Formula: C₃₃H₃₁F₂N₃O₂S
• Molecular Weight: 571.68
• Mol File: 174072-26-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 724.649°C at 760 mmHg
• Flash Point: 392.054°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 2-(4-Amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-7H-thieno[2,3-b]pyridin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-7H-thieno[2,3-b]pyridin-4-one(174072-26-5)
• EPA Substance Registry System: 2-(4-Amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-7H-thieno[2,3-b]pyridin-4-one(174072-26-5)

Safety Data

• Hazardous Substances Data: 174072-26-5(Hazardous Substances Data)

Usage

Synonyms

TDPU-332

Chemical Class

Thieno[2,3-b]pyridin-4-one derivative

Potential Applications

+ Calcium channel blocker
+ Treatment for cardiovascular diseases
+ Anti-inflammatory properties
+ Anti-tumor properties

Current Status

Being researched for potential therapeutic uses, requires further research and clinical trials to determine safety and efficacy for human use.

InChI:InChI=1/C33H31F2N3O2S/c1-20(2)30(39)26-19-38(18-24-27(34)10-7-11-28(24)35)33-29(31(26)40)25(17-37(3)16-21-8-5-4-6-9-21)32(41-33)22-12-14-23(36)15-13-22/h4-15,19-20H,16-18,36H2,1-3H3

Upstream product

• 174072-77-6 ethyl N-[3-carboxy-4-methyl-5-phenyl-2-thienyl]aminomethylenemalonate 
• 174070-98-5 ethyl 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylate 
• 174071-01-3 2-(4-aminophenyl)-3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174069-67-1 3-bromomethyl-7-(2,6-difluorobenzyl)-4,7-dihydro-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174069-42-2 ethyl 7-(2,6-difluorobenzyl)-4,7-dihydro-3-methyl-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylate 
• 174069-44-4 ethyl 7-(2,6-difluorobenzyl)-4,7-dihydro-3-methyl-4-oxo-2-phenylthieno[2,3-b]pyridine-5-carboxylate 
• 174072-80-1 ethyl 4-hydroxy-3-methyl-2-phenylthieno[2,3-b]pyridine-5-carboxylate 
• 697-73-4 2,6-difluorobenzyl chloride 
• 4815-38-7 ethyl 2-amino-4-methyl-5-phenylthiophene-3-carboxylate 
• 192886-68-3 3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2,6-difluorobenzyl)-2-(4-trifluoroacetylaminophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 192886-69-4 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide 
• 174072-73-2 2-[(3-ethoxycarbonyl-4-methyl-5-phenyl-thiophen-2-ylamino)-methylene]-malonic acid diethyl ester 
• 903520-54-7 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine 

Downstream Products

• 253434-13-8 4,7-dihydro-2-(4-N'-hydroxy-N'-methylureidophenyl)-7-(2,6-difluorobenzyl)-3-(N-benzyl-N-methylaminomethyl)-5-isobutyryl-4-oxothieno[2,3-b]pyridine 
• 253433-84-0 (R)-4,7-dihydro-2-[4-(3-t-butoxy-2-methylpropionylamino)phenyl]-7-(2,6-difluorobenzyl)-3-(N-benzyl-N-methylaminomethyl)-5-isobutyryl-4-oxothieno[2,3-b]pyridine 
• 253434-09-2 3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-5-isobutyryl-7-(2,6-difluorobenzyl)-2-(4-N'-methoxyureidophenyl)-4-oxothieno[2,3-b]pyridine 
• 903520-57-0 acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-cyclopropyl ester 
• 903520-56-9 ({4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-methyl)-carbamic acid tert-butyl ester 
• 253434-02-5 acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-1-methyl-ethyl ester 

Relevant articles and documents

Design, synthesis, and structure-activity relationships of thieno[2,3-b]pyridin-4-one derivatives as a novel class of potent, orally active, non-peptide luteinizing hormone-releasing hormone receptor antagonists

Design, synthesis, and structure-activity relationships of thieno[2,3-b]pyridin-4-one-based non-peptide luteinizing hormone-releasing hormone (LHRH) receptor antagonists are described. Starting with the thienopyridin-4-one derivative 26d (T-98475) an optimization study was performed, which resulted in the identification of a highly potent and orally bioavailable LHRH receptor antagonist, 3-(N-benzyl-N-methylaminomethyl)-7-(2,6- difluorobenzyl)-4,7-dihydro-2-[4-(1-hydroxy-1-cyclopropanecarboxamido)phen-yl] -5-isobutyryl-4-oxothieno[2,3-b]pyridine (33c). Compound 33c displayed subnanomolar in vitro activities for the human receptor and its oral administration caused effective suppression of the plasma LH levels in castrated male cynomolgus monkeys. Furthermore, SAR studies revealed that a hydroxyalkylamido moiety on the 2-phenyl ring is virtually equivalent to an alkylureido moiety, at least in this series of compounds.

Condensed-ring thiophene derivatives, their production and use

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