2-(4-Oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide

Base Information

• Chemical Name: 2-(4-Oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide
• CAS No.: 312946-37-5
• Molecular Formula: C₂₀H₁₆N₄O₂S₂
• Molecular Weight: 408.505
• European Community (EC) Number: 806-054-9
• NSC Number: 745843
• Nikkaji Number: J2.430.011K
• Pharos Ligand ID: SXVHLQTKX5M3
• ChEMBL ID: CHEMBL179945
• Mol file: 312946-37-5.mol

Synonyms:LDN-27219;312946-37-5;CHEMBL179945;2-(4-oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide;2-((4-oxo-3,5-diphenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)thio)acetohydrazide;2-({4-oxo-3,5-diphenyl-3H,4H-thieno[2,3-d]pyrimidin-2-yl}sulfanyl)acetohydrazide;ChemDiv1_004471;SCHEMBL6037616;HMS599L05;BDBM50163957;LDN 27219;NSC745843;STK838477;AKOS000673647;CS-3225;NSC-745843;NCGC00370696-05;HY-16693;F85050;EN300-6743236;SR-01000438687;SR-01000438687-1;Z56792612;(4-Oxo-3,5-diphenyl-3,4-dihydro-thieno[2,3-d]pyrimidin-2-ylsulfanyl)-acetic acid hydrazide;2-[(3,4-Dihydro-4-oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)thio]acetic acid hydrazide;2-[(4-oxo-3,5-diphenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)sulfanyl]acetohydrazide

Chemical Property of 2-(4-Oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide

Chemical Property:

• PKA: 11.87±0.37(Predicted)
• Density: 1.45±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble15mg/mL, clear
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 408.07146811
• Heavy Atom Count: 28
• Complexity: 617

Purity/Quality:

>98% ^*data from raw suppliers

LDN 27219 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CSC3=C2C(=O)N(C(=N3)SCC(=O)NN)C4=CC=CC=C4
• Uses: LDN 27219 is a transglutaminase inhibitor.

Technology Process of 2-(4-Oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide

There total 6 articles about 2-(4-Oxo-3,5-diphenylthieno[2,3-d]pyrimidin-2-yl)sulfanylacetohydrazide 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:

(4-oxo-3,5-diphenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylsulfanyl)acetic acid ethyl ester (312946-35-3) → LDN-27219 (312946-37-5)

Guidance literature:

With hydrazine; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2005.02.005

Reference yield:

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate (4815-36-5) → LDN-27219 (312946-37-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 50 °C

2: MeONa / methanol / 20 °C

3: K₂CO₃ / dimethylformamide / 20 °C

4: NH₂NH₂ / ethanol / 20 °C

With pyridine; sodium methylate; potassium carbonate; hydrazine; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.02.005

Reference yield:

4-Phenyl-2-(3-phenyl-thioureido)-thiophene-3-carboxylic acid ethyl ester (132605-18-6) → LDN-27219 (312946-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1: MeONa / methanol / 20 °C

2: K₂CO₃ / dimethylformamide / 20 °C

3: NH₂NH₂ / ethanol / 20 °C

With sodium methylate; potassium carbonate; hydrazine; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.02.005

upstream raw materials:

(4-oxo-3,5-diphenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylsulfanyl)acetic acid ethyl ester

ethyl 2-amino-4-phenyl-thiophene-3-carboxylate

4-Phenyl-2-(3-phenyl-thioureido)-thiophene-3-carboxylic acid ethyl ester

phenyl isothiocyanate

Refernces

• 1、 Duval, Eric,Case, April,Stein, Ross L.,Cuny, Gregory D.. "Structure-activity relationship study of novel tissue transglutaminase inhibitors". . p. 1885 - 1889. Retrieved 2007/10/03.