(+)-Blebbistatin

Base Information

• Chemical Name: (+)-Blebbistatin
• CAS No.: 1177356-70-5
• Molecular Formula: C₁₈H₁₆N₂O₂
• Molecular Weight: 292.337
• UNII: XWG1958E8I
• DSSTox Substance ID: DTXSID10424990
• Nikkaji Number: J2.122.916D
• Wikidata: Q27145266
• ChEMBL ID: CHEMBL1315589
• Mol file: 1177356-70-5.mol

Synonyms:(+)-Blebbistatin;1177356-70-5;(R)-(+)-Blebbistatin;Blebbistatin, (+)-;UNII-XWG1958E8I;XWG1958E8I;(3aR)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one;CHEBI:75387;(R)-3A-hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one;4H-Pyrrolo(2,3-b)quinolin-4-one, 1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-phenyl-, (3aR)-;(R)-blebbistatin;(+)-Brebbistatin;Tocris-1760;CHEMBL1315589;SCHEMBL15919292;DTXSID10424990;AKOS024456818;NCGC00025281-01;NCGC00381715-01;HY-107657;CS-0029060;J-003661;Q27145266;(3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one;(3aR)-(+)-1,2,3,3a-Tetrahydro-3a-hydroxy-6-methyl-1-phenyl-4H-pyrrolo[2,3-b]quinolin-4-one

Chemical Property of (+)-Blebbistatin

Chemical Property:

• PSA: 52.90000
• LogP: 2.36330
• Storage Temp.: -20C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 292.121177757
• Heavy Atom Count: 22
• Complexity: 497

Purity/Quality:

98% ^*data from raw suppliers

(R)-(+)-Blebbistatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)N=C3C(C2=O)(CCN3C4=CC=CC=C4)O
• Isomeric SMILES: CC1=CC2=C(C=C1)N=C3[C@@](C2=O)(CCN3C4=CC=CC=C4)O
• Uses: Blebbistatin blocked myosin II-dependent cell processes. It blocks cell blebbing rapidly and reversibly. Also rapidly disrupted directed cell migration and cytokinesis in vertebrate cell. It blocks both blebbing and cytokinesis at 50-100μM. A negative control for the (S)-(-)-Blebblastatin. [a]D= +110 (c= 1.21 CHCl3) (±)-1-Phenyl-1,2,3,4-tetrahydro-4-hydroxypyrrolo[2,3-b]-7-methylquinolin-4-one Selective inhibitor of nonmuscle myosin II; inhibits contraction of the cleavage furrow without disrupting mitosis or contractile ring assembly. Rapidly and reversibly blocks cell blebbing, and disrupts directed cell migration and cytokinesis in vertebrate cells.

Technology Process of (+)-Blebbistatin

There total 30 articles about (+)-Blebbistatin 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: 99.0%

1-(4-bromophenyl)-3a-hydroxy-6-methyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]quinolin-4-one (856925-74-1) → (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1002/ejoc.200500103

Reference yield: 37.0%

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9) → (3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8) + (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With (-)-(8,8-dichlorocamphorylsulfonyl)oxaziridine; In tetrahydrofuran; at -15 ℃; for 16h; Overall yield = 85%; Overall yield = 0.250 g; Inert atmosphere;

DOI:10.1039/c7ob00006e

Reference yield: 37.0%

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (856925-72-9) → (3aR)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8) + (3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one (1177356-70-5,674289-55-5,856925-71-8)

Guidance literature:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With (-)-(8,8-dichlorocamphorylsulfonyl)oxaziridine; In tetrahydrofuran; at -15 ℃; for 16h; Overall yield = 85%; Overall yield = 0.250 g; Inert atmosphere;

DOI:10.1039/c7ob00006e

upstream raw materials:

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one

1-phenylpyrrolidin-2-one

2-amino-5-methylbenzoic acid methyl ester

2-Amino-5-methylbenzoic acid

Downstream raw materials:

para-chloroblebbistatin

6-methyl-1-phenyl-1,2,3,9-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one