629652-40-0

Basic information

• Product Name: (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester
• Synonyms: (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester;(1S,3R)-1-(1;(1S,3R)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester;Tadalafil impurity 10
• CAS NO: 629652-40-0
• Molecular Formula: C₂₂H₁₉ClN₂O₅
• Molecular Weight: 425.84172
• Product Categories: Aromatics;Heterocycles;Indole Derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 629652-40-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 209 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 627.5±55.0 °C(Predicted)
• Appearance: /
• Density: 1.445±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 16.25±0.60(Predicted)
• CAS DataBase Reference: (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester(629652-40-0)
• EPA Substance Registry System: (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester(629652-40-0)

Safety Data

• Hazardous Substances Data: 629652-40-0(Hazardous Substances Data)

Usage

Uses

An intermediate in the preparation of cis-Tadalafil (T004520). A PDE5 inhibitor.

Upstream product

• 79-04-9 chloroacetyl chloride 
• 1039484-71-3 (3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester 

Downstream Products

• 171596-28-4 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione 
• 629652-72-8 (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1′,2’:1,6]-pyrido[3,4-b]indole-1,4-dione 
• 531500-48-8 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione 
• 531500-48-8 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione 
• 1018814-78-2 (6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-((R)-1-benzylpyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione 

Relevant articles and documents

Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 2. Tadalafil analogs

In this Letter we describe our ongoing target repurposing efforts focused on discovery of inhibitors of the essential trypanosomal phosphodiesterase TbrPDEB1. This enzyme has been implicated in virulence of Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). We outline the synthesis and biological evaluation of analogs of tadalafil, a human PDE5 inhibitor currently utilized for treatment of erectile dysfunction, and report that these analogs are weak inhibitors of TbrPDEB1.