CAS 126871-92-9

N(epsilon)-(diazotrifluoroethyl)benzoyl-Lys(8)-cyclosporin

Description:

N(epsilon)-(diazotrifluoroethyl)benzoyl-Lys(8)-cyclosporin, with CAS number 126871-92-9, is a synthetic derivative of cyclosporin, a cyclic peptide known for its immunosuppressive properties. This compound features a modification at the lysine residue, where a diazotrifluoroethyl group is attached to the epsilon amino group of lysine, enhancing its chemical reactivity and potentially altering its biological activity. The presence of the trifluoroethyl group may impart unique hydrophobic characteristics, influencing solubility and interaction with biological membranes. Cyclosporin itself is primarily used in organ transplantation and autoimmune diseases due to its ability to inhibit T-cell activation. The modification in this derivative may affect its pharmacokinetics, efficacy, and safety profile, making it a subject of interest in medicinal chemistry and drug development. As with many cyclosporin derivatives, understanding the structure-activity relationship is crucial for optimizing therapeutic applications while minimizing side effects.

Formula: C₇₄H₁₂₁F₃N₁₄O₁₃

InChI: InChI=1S/C74H121F3N14O13/c1-24-26-29-47(15)61(93)60-67(98)81-51(25-2)68(99)85(17)40-57(92)86(18)53(36-41(3)4)66(97)83-58(45(11)12)72(103)87(19)54(37-42(5)6)65(96)80-48(16)63(94)82-52(30-27-28-35-79-64(95)50-33-31-49(32-34-50)62(84-78)74(75,76)77)69(100)88(20)55(38-43(7)8)70(101)89(21)56(39-44(9)10)71(102)90(22)59(46(13)14)73(104)91(60)23/h24,26,31-34,41-48,51-56,58-61,93H,25,27-30,35-40H2,1-23H3,(H,79,95)(H,80,96)(H,81,98)(H,82,94)(H,83,97)

InChI key: InChIKey=MJGNMTOCIMTJOT-UHFFFAOYSA-N

SMILES: C(C(CC=CC)C)(O)C1N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CCCCNC(=O)C2=CC=C(C(C(F)(F)F)=[N+]=[N-])C=C2)NC(=O)C(C)NC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C(=O)C(CC)NC1=O

Synonyms:

• (E)-[(4E)-4-(1-diazonio-2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-ylidene][(4-{17-ethyl-14-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-4,7,10,13,19,22,28,32-octamethyl-11,26-bis(1-methylethyl)-5,8,23,29-tetrakis(2-methylpropyl)-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl}butyl)amino]methanolate
• 1,4,7,10,13,16,19,22,25,28,31-Undecaazacyclotritriacontane, cyclic peptide deriv.
• Csdz
• Cyclosporin A, 2-[N⁶-[4-(1-diazo-2,2,2-trifluoroethyl)benzoyl]-<span class="text-smallcaps">D</span>-lysine]-
• Cyclosporin A, 2-[N6-[4-(1-diazo-2,2,2-trifluoroethyl)benzoyl]-D-lysine]-
• N(epsilon)-(Diazotrifluoroethyl)benzoyl-lys(8)-cyclosporin