title: Synthesis and biological activities of some new (Nα-dinicotinoyl)-bis-L-leucyl linear and macrocyclic peptides.
abstract: A series of linear and macrocyclic peptides 3-12 were synthesized using 3,5-pyridinedicarboxylic acid (1) as starting material and screened for their antimicrobial, anti-inflammatory and anticancer activities. Bis-ester 3 was prepared from 1 and L-leucine methyl ester. Hydrazinolysis and hydrolysis of dipeptide methyl ester 3 with hydrazine hydrate or 1 N sodium hydroxide afforded compounds 4 and 5, respectively. Cyclization of the dipeptide 5 with L-lysine methyl ester afforded cyclic pentapeptide ester 6. Compounds 7-9 were synthesized by reacting hydrazide 4 with phthalic anhydride, 1,8-naphthalene anhydride or acetophenone derivatives. Treatment of acid hydrazide 4 with aromatic aldehydes or tetraacid dianhydrides afforded the corresponding bis-dipeptide hydrazones 10a-e and macrocyclic peptides 11 and 12, respectively. The structures of newly synthesized compounds were confirmed by IR, 1H-NMR, MS spectral data and elemental analysis. The detailed synthesis, spectroscopic data, biological and pharmacological activities of the synthesized compounds was reported.
authors: Chemistry Department, Faculty of Science for Girls, King Abdulaziz University, Jeddah 31534, Kingdom of Saudi Arabia. suzan.khayyat@yahoo.com.
authors: Suzan
authors: S
authors: Khayyat
authors: Pharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Kingdom of Saudi Arabia. aeamr1963@yahoo.com.
authors: Abd El-Galil
authors: Ael-G
authors: Amr
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005658:Fungi / Q000187:drug effects; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D010456:Peptides, Cyclic / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000494:pharmacology*; D011725:Pyridines / Q000737:chemistry; D051381:Rats; D023041:Xenograft Model Antitumor Assays
chemical_list: C546051:3,5-pyridinedicarboxylic acid; D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; D011725:Pyridines