Smad3 Inhibitor, SIS3

Base Information

• Chemical Name: Smad3 Inhibitor, SIS3
• CAS No.: 1009104-85-1
• Molecular Formula: C28H27N3O3
• Molecular Weight: 453.53
• Mol file: 1009104-85-1.mol

Synonyms:Smad3 Inhibitor, SIS3

Chemical Property of Smad3 Inhibitor, SIS3

Chemical Property:

• PSA: 56.59000
• LogP: 4.79350

Purity/Quality:

97% ^*data from raw suppliers

SMAD3 Inhibtor, SIS 3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: SMAD3 Inhibitor, SIS3 selectively inhibits TGF-β and activin. It has been shown to reduce TGF-β1-induced type 1 procollagen expression and myofibroblast differentiation in normal dermal fibroblasts as well as scleroderma fibroblasts.

Technology Process of Smad3 Inhibitor, SIS3

There total 19 articles about Smad3 Inhibitor, SIS3 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-iodo-1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine (945608-15-1) + 1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)prop-2-ene-1-one (245057-86-7) → ((E)-1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one) (1009104-85-1)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 200 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1021/jo070460b

Reference yield: 55.0%

3-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acrylic acid + 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride (2328-12-3) → SIS3 (1009104-85-1)

Guidance literature:

3-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acrylic acid; With oxalyl dichloride; In tetrahydrofuran; at 20 ℃; for 2h;

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

C12H16N2O3 (945608-26-4) → ((E)-1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)prop-2-en-1-one) (1009104-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1: PPh₃ / CH₂Cl₂ / 0 - 20 °C

2: 0.160 g / aq. HCl / 0.5 h / 75 °C

3: 84 percent / K₃PO₄*H₂O; S-Phos / Pd(OAc)2 / toluene / 2 h / 100 °C

4: 96 percent / N-iodosuccinimide / CH₂Cl₂ / 2.5 h / 0 - 20 °C

5: 90 percent / Bu₄NCl; Na₂CO₃ / Pd(OAc)2 / dimethylformamide / 0.08 h / 200 °C / microwave irradiation

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate; N-iodo-succinimide; tetrabutyl-ammonium chloride; sodium carbonate; triphenylphosphine; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide; toluene; 5: Heck reaction;

DOI:10.1021/jo070460b

upstream raw materials:

3-iodo-1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridine

1-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)prop-2-ene-1-one

[3-(2,2-dichlorovinyl)pyridin-2-yl]carbamic acid tert-butyl ester

C₁₂H₁₆N₂O₃