Detail of "39608-31-6"

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Design, synthesis and biological evaluation of cyclic angiotensin II analogs with 3,5 side-chain bridges role of C-terminal aromatic residue and ring cluster for activity and implications in the drug design of AT1 non-peptide antagonists

Design, synthesis and biological evaluation of cyclic angiotensin II analogs with 3,5 side-chain bridges role of C-terminal aromatic residue and ring cluster for activity and implications in the drug design of AT1 non-peptide antagonists. Roumelioti, Panagiota; Polevaya, Ludmila; Zoumpoulakis, Panagiotis; Giatas, Nektarios; Mutule, Ilze; Keivish, Tatjana; Zoga, Anastasia; Vlahakos, Demetrios; Iliodromitis, E.; Kremastinos, Demetrios; Grdadolnik, Simona Golic; Mavromoustakos, Thomas; Matsoukas, John (Department of Chemistry, University of Patras, Patras 26500, Greece). Bioorganic & Medicinal Chemistry Letters, 12(18), 2627-2633 (English) 2002 Elsevier Science Ltd. CODEN: BMCLE8.In this experiment, several chemicals are used like 4474-91-3 2389-45-9 and 39608-31-6 are cas registry numbers. These chemicals are also mentioned in this article. ISSN: 0960-894X. DOCUMENT TYPE: Journal CA Section: 34 (Amino Acids, Peptides, and Proteins) Section cross-reference(s): 1, 22 The novel amide linked Angiotensin II (ANG II) cyclic analogs: g,e-cyclo(3, 5)-[Sar1-Glu3-Lys5-Ile8] ANG II (I) and g, e-cyclo(3, 5)-[Sar1-Glu3-Lys5-Phe8] ANG II (II) have been designed, synthesized and bioassayed in anesthetized rabbits in order to unravel structural ring cluster characteristics important for receptor activation. Analog I with Ile at position 8 was an inhibitor of Angiotensin II while analog II with Phe at position 8 was found to be an agonist. Similar results were reported for cyclic compds. that have reversed the linking between positions 3 and 5. The overall results show that positions 3 and 5 do not govern the biol. activity of the synthetic analogs. It also appears that the arom. ring cluster (Tyr-His-Phe) in agonist peptides is an essential stereo-electronic feature for Angiotensin II to exert its biol. activity. A non-peptide mimetic of ANG II, 1-[2'-[(N-benzyl)tetrazol-5-yl]biphenyl-4-yl]methyl-2-hydroxymethylbenzim idazole (BZI8) has been designed and synthesized. This mol. is more rigid and much less active than AT1 non-peptide mimetic losartan probably because it lacks to mimic the orientation of tetrazole and the pharmacophore segments of Bu chain and imidazole ring. ..

Angiotensin II analogs

Angiotensin II analogs. Part II. Synthesis and incorporation of the sulfur-containing aromatic amino acids: L-(4'-SH)Phe, L-(4'-SO2NH2)Phe, L-(4'-SO3-)Phe and L-(4'-SCH3)Phe. Escher, Emanuel; Bernier, Michel; Parent, Paul (Fac. Med.Chemicals with cas numbers 88170-94-9 and 39608-31-6 also play role., Univ. Sherbrooke, Sherbrooke, PQ J1H 5NH, Can.). Helv. Chim. Acta, 66(5), 1355-65 (English) 1983. CODEN: HCACAV. ISSN: 0018-019X. DOCUMENT TYPE: Journal CA Section: 34 (Amino Acids, Peptides, and Proteins) Section cross-reference(s): 2 L-Phenylalanine (I, R = H) was treated with ClSO3H to give I (R = SO2Cl) (II), which was hydrolyzed and amidated in situ to give I (R = SO3H and SO2NH2, resp.), which were converted to the corresponding N-tert-butoxycarbonyl (N-Boc) derivs. II was reduced to give I (R = SH), which was converted to phenylalanines III [R1 = Boc, SCMe3, SC6H4Me-p, CH2NHAc (Acm), CH2Ph, CH2C6H4Br-m, Me]. The above compds. were used in the solid-phase synthesis of angiotensin II analogs IV (Sar = MeGly; R2 = SO3H, SO2NH2, SAcm, SH) and V (X = Sar, R2 = SAcm, SH; X = Asp, R2 = SAcm). IV and V were used for structure-activity relationship studies in 3 different bioassays; IV (R2 = SO3H) was a complete nonagonist in all 3 bioassays, whereas V (X = Sar, R2 = SAcm) was a potent antagonist on rabbit aorta. .