(-)-Blebbistatin

Base Information

• Chemical Name: (-)-Blebbistatin
• CAS No.: 856925-71-8
• Molecular Formula: C₁₈H₁₆N₂O₂
• Molecular Weight: 292.337
• European Community (EC) Number: 689-630-0
• UNII: 8WII7624I5
• DSSTox Substance ID: DTXSID70415329
• Nikkaji Number: J2.122.915F
• Wikidata: Q27093043
• Metabolomics Workbench ID: 146559
• ChEMBL ID: CHEMBL1231358
• Mol file: 856925-71-8.mol

Synonyms:(-)-Blebbistatin;856925-71-8;(S)-(-)-Blebbistatin;Blebbistatin, (-)-;(S)-blebbistatin;(-)Blebbistatin;Blebbistatin (S)-form [MI];CHEBI:75388;UNII-8WII7624I5;CHEMBL1231358;8WII7624I5;(S)-3a-hydroxy-6-methyl-1-phenyl-3,3a-dihydro-1H-pyrrolo[2,3-b]quinolin-4(2H)-one;(-)-1-PHENYL-1,2,3,4-TETRAHYDRO-4-HYDROXYPYRROLO[2,3-B]-7-METHYLQUINOLIN-4-ONE;4H-Pyrrolo(2,3-b)quinolin-4-one, 1,2,3,3a-tetrahydro-3a-hydroxy-6-methyl-1-phenyl-, (3aS)-;1,2,3,3a-Tetrahydro-3aS-hydroxy-6-methyl-1-phenyl-4H-Pyrrolo[2,3-b]quinolin-4-one;(3aS)-3a-hydroxy-6-methyl-1-phenyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one;blebbistatin-(-);(?)-Blebbistatin;MFCD08460907;blebbistatin-(+/-);SCHEMBL4330341;DTXSID70415329;EX-A703;HMS3648O21;HMS3653A05;HMS3674I13;BCP09979;(-)-Blebbistatin, solid, synthetic;BDBM50546882;s7099;AKOS024456817;CCG-267396;CS-4983;DB01944;NCGC00092288-01;NCGC00092288-02;NCGC00092288-05;AC-35899;AS-57305;BB181114;HY-13441;SW219535-1;F17375;SR-01000946255;SR-01000946255-1;Q27093043;(3aS)-3a-hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one;(3aS)-3a-hydroxy-6-methyl-1-phenyl-1H,2H,3H,3aH,4H-pyrrolo[2,3-b]quinolin-4-one;(S)-3a-Hydroxy-6-methyl-1-phenyl-1,2,3,3a-tetrahydro-4H-pyrrolo[2,3-b]quinolin-4-one;(3aS)-(-)-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:

• Melting Point: 210-212°C
• Boiling Point: 507.3±60.0 °C(Predicted)
• PKA: 11.15±0.20(Predicted)
• PSA: 52.90000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 1.61050
• Storage Temp.: Desiccate at +4°C
• Solubility.: DMSO: soluble5mg/mL
• 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:

99% ^*data from raw suppliers

(S)-(-)-Blebbistatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37

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]D= -103 (?)-Blebbistatin has been used to investigate the effect on cardiac contractility and effect of thrombin on actomyosin contractility

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-(4-bromophenyl)-3a-hydroxy-6-methyl-1,2,3,3a-tetrahydropyrrolo[2,3-b]quinolin-4-one

1-(4-bromophenyl)-6-methyl-1,2,3,9-tetrahydropyrrolo[2,3-b]quinolin-4-one

1-phenylpyrrolidin-2-one

Downstream raw materials:

para-chloroblebbistatin

Refernces

Insights into the myosin II inhibitory potency of A-ring-modified (S)-blebbistatin analogs

10.1016/j.bmcl.2017.05.008

The study investigates the myosin II inhibitory potency of (S)-blebbistatin analogs with modified A-rings. Myosin II is a target for therapeutic intervention due to its involvement in motility-based diseases. The researchers synthesized a series of (S)-blebbistatin derivatives, including (S)-benzo[h]blebbistatin (S)-2, (S)-(1H)-pyrrolo[3,2-h]blebbistatin (S)-3, (S)-(2,3-dihydro-1H)-pyrrolo[3,2-h]blebbistatin (S)-4, and (S)-(N-allyl-2,3-dihydro-1H)-pyrrolo[3,2-h]blebbistatin (S)-5, to explore how modifications to ring A affect inhibitory potency. The compounds were evaluated in a steady-state ATPase assay using rabbit skeletal muscle myosin II, with (S)-blebbistatin (S)-1 as a benchmark. The results showed that extending the aromatic system of ring A or incorporating aliphatic ring systems did not enhance binding affinity, indicating that potency enhancement via ring A modification is unlikely. The study concludes that future attempts to improve (S)-blebbistatin's potency should focus on ring C.