171596-28-4

Basic information

• Product Name: cis-ent-Tadalafil
• Synonyms: cis-ent-Tadalafil;(6S,12aR)-;Tadalafil IMpurity: IMpurity F;Tadalafil EP IMpurity C (cis-ent-tadalafil);Tadalafil IMpurity E (6S, 12R);(6S,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;Tadanafil EP or USP impurity C;Tadalafil Impurity C (cis-ent-Tadalafil)
• CAS NO: 171596-28-4
• Molecular Formula: C₂₂H₁₉N₃O₄
• Molecular Weight: 388.39602
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 171596-28-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 287-289 °C(Solv: toluene (108-88-3))
• Boiling Point: 679.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 16.68±0.40(Predicted)
• CAS DataBase Reference: cis-ent-Tadalafil(CAS DataBase Reference)
• NIST Chemistry Reference: cis-ent-Tadalafil(171596-28-4)
• EPA Substance Registry System: cis-ent-Tadalafil(171596-28-4)

Safety Data

• Hazardous Substances Data: 171596-28-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 171596-28-4 differently. You can refer to the following data:
1. The (6S)-cis-enantiomer of Tadalafil (T004500). Tadalafil Impurity (6S,12aR)
2. The (6S)-cis-enantiomer of Tadalafil (T004500).

Upstream product

• 50-00-0 formaldehyd 
• 120-57-0 piperonal 
• 593-51-1 methylamine hydrochloride 
• 5241-64-5 Boc-D-Trp-OH 
• 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 
• 74-89-5 methylamine 
• 629652-40-0 (1S,3R)-1-benzo[1,3]dioxol-5-yl-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 749864-19-5 1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 79-04-9 chloroacetyl chloride 
• 1422164-52-0 (R)-ethyl 2-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)-N-methylpropanamido)acetate 
• 1422164-53-1 (R)-3-((1H-indol-3-yl)methyl)-1-methylpiperazine-2, 5-dione 
• 1321600-91-2 methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 
• 171596-42-2 (1S,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester 
• 4299-70-1 D-Tryptophan methyl ester 

Downstream Products

• 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 

Relevant articles and documents

Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: A synthetic route towards cialis analogues

A facile and efficient synthetic method for the stereoselective preparation of trisubstituted tetrahydro-β-carboline-fused diketopiperazine derivatives is reported. The methodology represents a one-pot four-step reaction, employing the Ugi four-component

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.

An efficient and general method for the stereodivergent syntheses of tadalafil-like tetracyclic compounds

A clean and general DBU-catalyzed epimerization at C-12a position of the tadalafil-like tetracyclic compounds has been fully studied. In addition, by using this clean epimerization as the key step, four stereomers of 6-d 1-tadalafil were stereodivergently synthesized from, both L- and D-tryptophan methyl ester hydrochlorides and deuterated piperonal.