74588-78-6

Basic information

• Product Name: (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE
• Synonyms: D-64131;(5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE;D-6413;D-64131(sc-203908)
• CAS NO: 74588-78-6
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Product Categories: Caspases/Apoptosis;Inhibitors
• Mol File: 74588-78-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 162 °C
• Boiling Point: 455.2°C at 760 mmHg
• Flash Point: 229.1°C
• Appearance: /
• Density: 1.231g/cm³
• Vapor Pressure: 1.79E-08mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Store at RT
• Solubility: Soluble in DMSO
• PKA: 14.81±0.30(Predicted)
• CAS DataBase Reference: (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE(74588-78-6)
• EPA Substance Registry System: (5-METHOXY-1H-INDOL-2-YL)PHENYLMETHANONE(74588-78-6)

Safety Data

• Hazardous Substances Data: 74588-78-6(Hazardous Substances Data)

Usage

Uses

Novel inhibitor of tubulin polymerization

Biological Activity

Novel inhibitor of tubulin polymerization; cytotoxic and inhibits tumor cell proliferation in vitro (IC 50 = 74 nM). Prevents growth of tumor models in mice following oral administration in vivo .

references

1. beckers t, reissmann t, schmidt m et al. 2-aroylindoles, a novel class of potent, orally active small molecule tubulin inhibitors. cancer res. 2002 jun 1;62(11):3113-9.

InChI:InChI=1/C16H13NO2/c1-19-13-7-8-14-12(9-13)10-15(17-14)16(18)11-5-3-2-4-6-11/h2-10,17H,1H3

Upstream product

• 74588-94-6 5-Methoxy-1-(2-oxo-2-phenyl-ethyl)-1H-indole-2,3-dione 
• 74588-83-3 5-methoxy-2-benzoylindolyl-3-carboxylic acid 
• 370580-32-8 (5-methoxy-1-phenylsulfonyl-1H-2-indolyl)-phenylmethanone 
• 21778-81-4 5-methoxy-1H-indole-2-carbaldehyde 
• 1006-94-6 5-methoxylindole 
• 56995-12-1 1-benzenesulfonyl-5-methoxy-1H-indole 
• 370580-14-6 (5-methoxy-1-phenylsulfonyl-1H-2-indolyl)-phenylmethanol 
• 100-52-7 benzaldehyde 
• 39755-95-8 5-methoxyisatine 
• 1252576-12-7 N-(2-(chloromethyl)-4-methoxyphenyl)-4-methylbenzenesulfonamide 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 675578-41-3 N-(2-(hydroxymethyl)-4-methoxyphenyl)-4-methylbenzenesulfonamide 
• 1619222-63-7 C₁₆H₁₃BrO₂ 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 

Downstream Products

• 622863-59-6 9-methoxy-4,5-diphenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 
• 622863-61-0 9-methoxy-4-methyl-5-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 
• 622863-66-5 9-methoxy-5-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione 
• 622863-58-5 2-[(E)-1,2-diphenylethenyl]-5-methoxy-1H-indole 
• 622863-60-9 (E)-5-methoxy-2-(1-phenylprop-1-en-1-yl)-1H-indole 
• 135554-08-4 methyl 2-(1-phenylvinyl)-1H-indol-5-yl ether 

Relevant articles and documents

Palladium-catalyzed tandem oxidative annulation of α-amino ketones leading to 2-aroylindoles

A simple synthesis of 2-aroylindoles via palladium-catalyzed tandem oxidative annulation directly from α-amino ketones has been developed. In this transformation, two-step reaction including oxidation of α-amino aetones to generate imine intermediates and

Cp*Co(iii)-catalysed selective alkylation of C-H bonds of arenes and heteroarenes with α-diazocarbonyl compounds

Cp*Co(iii)-catalysed selective alkylation of directed C-H bonds of arenes and heteroarenes has been accomplished employing donor-acceptor carbenes, derived from α-diazocarbonyl compounds. The developed method allows ready access to various substituted α-(hetero)aryl-α-arylacetic acid derivatives in good to excellent yields. Synthetic utility was also shown through the synthesis of a substituted indole derivative, an anticancer agent.

A new approach to 1-substituted β-carbolines and isoquinolines utilizing tributyl[(Z)-2-ethoxyvinyl]stannane as a C-3,C-4 building block

Starting from readily available indole-2-carboxylic acids, 1-substituted β-carbolines (among them the alkaloids harmane and isoharmine) are readily obtained via the corresponding 2-acylindoles, bromination at C-3, followed by a one-pot Stille cross-coupling with tributyl[(Z)-2-ethoxyvinyl]stannane, and ring closure with ammonium acetate. 1-Substituted isoquinolines are available in an analogous manner starting from 2-bromobenzoic acid.