113811-42-0

Basic information

• Product Name: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid
• Synonyms: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid
• CAS NO: 113811-42-0
• Molecular Formula: C₁₇H₁₉N₈O₆P
• Molecular Weight: 462.36
• Mol File: 113811-42-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.72g/cm³
• Refractive Index: 1.786
• CAS DataBase Reference: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid(113811-42-0)
• EPA Substance Registry System: 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid(113811-42-0)

Safety Data

• Hazardous Substances Data: 113811-42-0(Hazardous Substances Data)

Usage

General Description

2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid is a chemical compound with the molecular formula C19H19N7O6P. It is a derivative of folic acid and is commonly used as an antifolate agent in the treatment of certain types of cancer, including leukemia and lymphoma. The compound works by interfering with the production of DNA and RNA in cancer cells, ultimately leading to the inhibition of cell growth and division. Additionally, it has been studied for its potential use in the treatment of autoimmune disorders and has shown promise in the management of rheumatoid arthritis and psoriasis. Despite its potential therapeutic benefits, 2-[[4-[(2,4-diaminopteridin-6-yl)methylamino]benzoyl]amino]-3-phosphon o-propanoic acid can have significant side effects, including gastrointestinal issues, bone marrow suppression, and liver toxicity, and should be used under the guidance of a healthcare professional.

InChI:InChI=1/C17H19N8O6P/c18-13-12-14(25-17(19)24-13)21-6-10(22-12)5-20-9-3-1-8(2-4-9)15(26)23-11(16(27)28)7-32(29,30)31/h1-4,6,11,20H,5,7H2,(H,23,26)(H,27,28)(H2,29,30,31)(H4,18,19,21,24,25)

Upstream product

• 95485-01-1 p-nitrophenyl 4-amino-4-deoxy-N¹⁰-formylpteroate 
• 113811-52-2 benzyl DL-2-amino-3-phosphonopropanoate 

Relevant articles and documents

Methotrexate analogues. 32. Chain extension, α-carboxyl deletion, and γ-carboxyl replacement by sulfonate and phosphonate: Effect on enzyme binding and cell-growth inhibition

Analogues of methotrexate (MTX) and aminopterin (AMT) with aminophosphonoalkanoic, aminoalkanesulfonic, and aminoalkanephosphonic acid side chains in place of glutamate were synthesized and tested as inhibitors of folylpolyglutamate synthetase (FPGS) from mouse liver. The aminophosphonoalkanoic acid analogues were also tested as inhibitors of dihydrofolate reductase (DHFR) from L1210 murine leukemia cells and as inhibitors of the growth of MTX-sensitive (L1210) and MTX-resistant (L1210/R81) cells in culture. The optimal number of CH2 groups in aminophosphonoalkanoic acid analogues of AMT was found to be two for both enzyme inhibition and cell growth inhibition but was especially critical for activity against FPGS. Deletion of the α-carboxyl also led to diminished anti-FPGS activity in comparison with previously studied homocysteic acid and 2-amino-4-phosphonobutyric acid analogues. In the aminoalkanesulfonic acid analogues of MTX without an α-carboxyl, anti-FPGS activity was low and showed minimal variation as the number of CH2 groups between the carboxamide and sulfonate moieties was changed from one to four. In similar aminoalkanephosphonic acid analogues of MTX, anti-FPGS activity was also low, was comparable for two and three CH2 groups between the carboxamide and phosphonate moieties, and was diminished by monoesterification of the phosphonate group. These effects demonstrate that the α-carboxyl group of folate analogues is involved in binding to the active site of FPGS, and that an α-carboxyl group should be retained as part of the structure of FPGS inhibitors.