142165-63-7

Basic information

• Product Name: 1H-INDOLE-1,5-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(PHENYLMETHYL)ESTER
• Synonyms: 1H-INDOLE-1,5-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(PHENYLMETHYL)ESTER
• CAS NO: 142165-63-7
• Molecular Formula: C₁₇H₁₅NO₄
• Molecular Weight: 297.31
• Mol File: 142165-63-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 509.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.348±0.06 g/cm3(Predicted)
• PKA: 4.45±0.20(Predicted)
• CAS DataBase Reference: 1H-INDOLE-1,5-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(PHENYLMETHYL)ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-INDOLE-1,5-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(PHENYLMETHYL)ESTER(142165-63-7)
• EPA Substance Registry System: 1H-INDOLE-1,5-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(PHENYLMETHYL)ESTER(142165-63-7)

Safety Data

• Hazardous Substances Data: 142165-63-7(Hazardous Substances Data)

Usage

Molecular weight

297.31 g/mol

Physical state

White crystalline solid

Chemical class

Indole derivatives

Common uses

Building block for the synthesis of various drugs and pharmaceutical products

Therapeutic potential

Treatment of neurological disorders and cancer

Research applications

Precursor for the synthesis of novel organic molecules with potential biological activities.

Upstream product

• 15861-30-0 2,3-dihydro-1H-indole-5-formic acid 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 142165-64-8 (S)-2-[(1-Benzyloxycarbonyl-2,3-dihydro-1H-indole-5-carbonyl)-amino]-pentanedioic acid diethyl ester 
• 142165-67-1 (S)-2-[(1-Benzyloxycarbonyl-2,3-dihydro-1H-indole-5-carbonyl)-amino]-hexanedioic acid dimethyl ester 
• 142166-28-7 methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-(3-ethoxycarbonylphenyl)-L-glutaminate 
• 142165-90-0 methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-(3-ethoxycarbonylphenyl)-L-glutaminate 
• 194206-09-2 methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-[2-(ethoxycarbonyl)cyclopropylcarbonyl]-L-ornithinate 
• 142166-24-3 methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-phenyl-L-glutaminate 
• 194206-08-1 methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-succinyl-L-ornithinate 
• 142165-83-1 methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-phenyl-L-glutaminate 
• 142165-94-4 methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-dimethyl-L-glutaminate 
• 142165-91-1 3-{(S)-4-[(2,3-Dihydro-1H-indole-5-carbonyl)-amino]-4-methoxycarbonyl-butyrylamino}-benzoic acid ethyl ester 
• 142165-84-2 (S)-2-[(2,3-Dihydro-1H-indole-5-carbonyl)-amino]-4-phenylcarbamoyl-butyric acid methyl ester 
• 156578-52-8 5-Chlorocarbonyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester 

Relevant articles and documents

Antirheumatic agents. I. Novel methotrexate derivatives bearing an indoline moiety

Various novel methotrexate (MTX) derivatives bearing an indoline moiety were synthesized and tested for biological activities using human peripheral blood mononuclear cell (hPBMC) and human synovial cells (hSC) derived from patients with rheumatoid arthritis (RA). Compounds having potent activity in vitro were further evaluated using an adjuvant arthritis model in vivo. N- [1-(2,4-Diamino-6-pteridinylmethyl)indoline-5-carbonyl]-L-glutamic acid 2f showed more potent activities than MTX in vitro and in vivo, and N-[1-(2,4- diamino-6-pteridinylmethyl)-indoline-5-carbonyl]-L-2-aminoadipic acid 2d exhibited fairly good activities in vitro and considerable activity in vivo. Compound 2d was, as expected, not sensitive to folyl-polyglutamate synthetase (FPGS) and did not undergo polyglutamation, a process which may be responsible for a side-effect during MTX therapy.