FC 131

Base Information

• Chemical Name: FC 131
• CAS No.: 606968-52-9
• Molecular Formula: C36H47N11O6
• Molecular Weight: 729.83
• Mol file: 606968-52-9.mol

Synonyms:Cyclo[3-(2-naphthalenyl)-L-alanylglycyl-D-tyrosyl-L-arginyl-L-arginyl]

Chemical Property of FC 131

Chemical Property:

• PKA: 9.89±0.15(Predicted)
• PSA: 289.53000
• Density: 1.45±0.1 g/cm3(Predicted)
• LogP: 2.95200

Purity/Quality:

97% ^*data from raw suppliers

Cyclo[3-?(2-?naphthalenyl)?-?L-?alanylglycyl-?D-?tyrosyl-?L-?arginyl-?L-?arginyl] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: C-X-C chemokine receptor 4 (CXCR4) is a receptor for the stromal cell-derived factor-1 (SDF-1) which is designated as chemokine ligand 12 (CXCL12). It is involved in cell progression, hematopoiesis, cancer, HIV entry, and rheumatoid arthritis. FC 131 is an inhibitor of CXCR4 activation by SDF-1 (IC50 = 4.5 nM) and also blocks HIV-induced cytopathogenicity (EC50 = 73 nM). FC 131 derivatives can be used for imaging CXCR4 and elucidating its function.
• Uses: Cyclo[3-?(2-?naphthalenyl)?-?L-?alanylglycyl-?D-?tyrosyl-?L-?arginyl-?L-?arginyl] is a CXCR4 antagonist with anti-HIV properties.

Technology Process of FC 131

There total 4 articles about FC 131 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:

C45H59N15O8 → cyclo(-D-Tyr1-L-Arg2-L-Arg3-L-[3-(2-naphthyl)alanine]4-Gly5-) (606968-52-9)

Guidance literature:

C₄₅H₅₉N₁₅O₈; With hydrogenchloride; isopentyl nitrite; In water; N,N-dimethyl-formamide; at -20 ℃; for 0.5h;

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at -20 - 20 ℃; for 2h; Cooling;

DOI:10.1016/j.bmcl.2018.03.027

Reference yield:

C66H87N11O12S2 → cyclo(-D-Tyr1-L-Arg2-L-Arg3-L-[3-(2-naphthyl)alanine]4-Gly5-) (606968-52-9)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1.5h;

DOI:10.1039/b908286g

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-D-Tyr(O-tBu)-OH (118488-18-9,204384-67-8) + N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine (138774-94-4,186320-03-6) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → cyclo(-D-Tyr1-L-Arg2-L-Arg3-L-[3-(2-naphthyl)alanine]4-Gly5-) (606968-52-9)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm0607350

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-D-Tyr(O-tBu)-OH

N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine