Lometrexol

Base Information

• Chemical Name: Lometrexol
• CAS No.: 106400-81-1
• Molecular Formula: C₂₁H₂₅N₅O₆
• Molecular Weight: 443.459
• Mol file: 106400-81-1.mol

Synonyms:L-Glutamicacid, N-[4-[2-(2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl]-,(R)-; L-Glutamic acid,N-[4-[2-[(6R)-2-amino-1,4,5,6,7,8-hexahydro-4-oxopyrido[2,3-d]pyrimidin-6-yl]ethyl]benzoyl]-(9CI); Pyrido[2,3-d]pyrimidine, L-glutamic acid deriv.; LY 264618; Lometrexol

Chemical Property of Lometrexol

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 3.60±0.10(Predicted)
• Flash Point: °C
• PSA: 187.50000
• Density: 1.56g/cm³
• LogP: 1.72700
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥5mg/mL

Purity/Quality:

97% ^*data from raw suppliers

Lometrexol hydrate ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Description: Glycinamide ribonucleotide formyltransferase (GART) is a folate-dependent enzyme required for de novo purine synthesis. Lometrexol is a folate analog antimetabolite with antineoplastic activity. At nanomolar conentrations, it inhibits GART preventing de novo purine synthesis, inhibiting DNA synthesis, arresting cells in the S phase of the cell cycle, and inhibiting tumor cell proliferation.
• Uses: Lometrexol hydrate was used to compare the biological activity of potent inhibitor of human GARFTase. It is an antifolate which inhibits glycinamide ribonucleotide formyltransferase (GARFT), an enzyme essential for de novo purine synthesis.

Technology Process of Lometrexol

There total 33 articles about Lometrexol 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: 69.0%

2-{4-[2-(2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester → lometrexol (95693-76-8,106400-18-4,106400-81-1,135503-66-1)

Guidance literature:

With sodium hydroxide; In methanol; at 23 - 25 ℃; for 48h;

DOI:10.1021/jm00119a018

Reference yield:

(6S)-2-amino-4-hydroxy-6-[2-(4-bromophenyl)ethyl]-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine + 2-chloro-4,6-dimethoxy-1 ,3,5-triazine (3140-73-6) + (6R)-2-amino-4hydroxy-6-[2-(4-carboxyphenyl)ethyl]-5,6,7,8-tetrahydropyrido 2,3-d]pyrimidine hydrochloride + diethyl-L-glutamate hydrochloride (1118-89-4) → lometrexol (95693-76-8,106400-18-4,135503-66-1,106400-81-1)

Guidance literature:

With 4-methyl-morpholine; In N-methyl-acetamide; sodium hydroxide; ethanol;

Reference yield:

diethyl N-<4-<2-(2-amino-1,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethenyl>benzoyl>-L-glutamate → lometrexol (95693-76-8,106400-18-4,106400-81-1,135503-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, HCl / PtO₂ / methanol / 20 h / 2637.5 Torr

2: 69 percent / NaOH / methanol / 48 h / 23 - 25 °C

With hydrogenchloride; sodium hydroxide; hydrogen; platinum(IV) oxide; In methanol;

DOI:10.1021/jm00119a018

upstream raw materials:

(S)-2-{4-[2-((R)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid diethyl ester

L-glutamic acid

(R)-(-)-4-<2-(2-Amino-1,4,5,6,7,8-hexahydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethyl>benzonic acid

diethyl-L-glutamate hydrochloride