142165-63-7

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

• 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 
• 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 

Relevant academic research and scientific papers

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.

Methotrexate derivative

Disclosed is a compound represented by the formula: STR1 wherein R1 : CH2, CH2 CH2, CH2 O, CH2 S, CH2 SO; R2 : hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or a benzyl group; n: an integer of 1 to 4; R3 : COOR4, NHCOR5, CONR6 R7, PO3 H2, SO3 H. The compound shows potent antirheumatic function, psoriasis curing function and carcinostatic function and has low toxicity whereby it is available as a medicine.