N-Methylleukotriene C4

Base Information

• Chemical Name: N-Methylleukotriene C4
• CAS No.: 131391-65-6
• Molecular Weight: 639.8
• Mol file: 131391-65-6.mol

Synonyms:N-[S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-Carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetren-1-yl]-N-(L-γ-glutamyl)-L-cysteinyl]-N-methylglycine;N-Methylleukotriene C4;NMLTC4;N-METHYL LTC4

Chemical Property of N-Methylleukotriene C4

Chemical Property:

• Boiling Point: 965.7±65.0 °C(Predicted)
• PKA: 2.23±0.10(Predicted)
• Density: 1.202±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

N-methylLeukotrieneC4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Produced by neutrophils, macrophages, mast cells, and by transcellular metabolism in platelets, leukotriene C4 (LTC4) is the parent cysteinyl leukotriene formed by the LTC4 synthase-catalyzed conjugation of glutathione to LTA4. It is one of the constituents of slow-reacting substance of anaphylaxis (SRS-A) and exhibits potent smooth muscle contracting activity. LTC4, however, is rapidly metabolized to LTD4 and LTE4, which makes the characterization of LTC4 pharmacology difficult. N-methyl Leukotriene C4 (N-methyl LTC4) is a synthetic analog of LTC4 that is not readily metabolized to LTD4 and LTE4.It acts as a potent and selective CysLT2 receptor agonist exhibiting EC50 values of 122 and > 2,000 nM at the human CysLT2 and CysLT1 receptors, respectively. It has essentially the same potency as LTC4 at both the human and murine receptors CysLT2 receptors. N-methyl LTC4 is potent and active in vivo, causing vascular leak in mice overexpressing the human CysLT2 receptor but not in CysLT2 receptor knockout mice. N-methyl Leukotriene C4 is synthetic analog of LTC4 with decreased binding affinity.

Technology Process of N-Methylleukotriene C4

There total 5 articles about N-Methylleukotriene C4 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:

N-methyl LTC4 dimethyl ethyl ester → N-methyl LTC4 (131391-65-6)

Guidance literature:

With tempol; potassium carbonate; In methanol; water; for 48h;

DOI:10.1021/jo00058a049

Reference yield:

LTA4 ethyl ester → N-methyl LTC4 (131391-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / triethylamine, 4-hydroxytempo / methanol

2: 76 percent / dioxane / 0.67 h / Irradiation

3: 33 percent Spectr_. / K₂CO₃, 4-hydroxytempo / methanol; H₂O / 48 h

With tempol; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; water;

DOI:10.1021/jo00058a049

Reference yield:

(S)-4-[(R)-2-Mercapto-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-2-[methyl-(2-nitro-benzyl)-amino]-butyric acid methyl ester (146963-37-3) → N-methyl LTC4 (131391-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / triethylamine, 4-hydroxytempo / methanol

2: 76 percent / dioxane / 0.67 h / Irradiation

3: 33 percent Spectr_. / K₂CO₃, 4-hydroxytempo / methanol; H₂O / 48 h

With tempol; potassium carbonate; triethylamine; In 1,4-dioxane; methanol; water;

DOI:10.1021/jo00058a049

upstream raw materials:

(S)-4-[(R)-2-Mercapto-1-(methoxycarbonylmethyl-carbamoyl)-ethylcarbamoyl]-2-[methyl-(2-nitro-benzyl)-amino]-butyric acid methyl ester

C₄₀H₅₄N₈O₁₆S₂

Refernces