Reference

Synthesis and photobiological activity of N-substituted 2-oxo-2H-1-benzopyran-3-(thio)carboxamides

Synthesis and photobiological activity of N-substituted 2-oxo-2H-1-benzopyran-3-(thio)carboxamides. El-Ahmad, Youssef; Brion, Jean-Daniel; Reynaud, Pierre; Averbeck, Dietrich; Averbeck, Simone (Laboratoire Chimie Therapeutique, Faculte Pharmacie, Chatenay-Malabry 92296, Fr.). 2038-03-1 and 148-53-8 are cas registry numbers. These chemicals are also mentioned in this article. Heterocycles, 43(10), 2169-2177 (English) 1996 Japan Institute of Heterocyclic Chemistry. CODEN: HTCYAM. ISSN: 0385-5414. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 1, 10 Several polyfunctional coumarins I (R1, R2, R3 = H, OMe; NR42 = NMe2, NEt2, morpholino; X = O, S) and the corresponding quaternary ammoniums, assocd. with a coplanar structure, have been synthesized in order to test the relationships between structure and photobiol. activity. In vitro studies on their phototoxic effects in yeasts suggest that five of them are able to intercalate in DNA and to covalently photobind to DNA. .

Enantiomerically Pure Isophorone Diamine [3-(Aminomethyl)-3,5,5-trimethylcyclohexylamine]: A Chiral 1,4-Diamine Building Block Made Available on Large Scale

All Rights Reserved. Enantiomerically Pure Isophorone Diamine [3-(Aminomethyl)-3,5,5-trimethylcyclohexylamine]: A Chiral 1,4-Diamine Building Block Made Available on Large Scale. Berkessel, Albrecht; Roland, Katrin; Schroeder, Michael; Neudoerfl, Joerg M.; Lex, Johann (Institut fuer Organische Chemie, Universitaet zu Koeln, Cologne D-50939, Germany). Journal of Organic Chemistry, 71(25), 9312-9318 (English) 2006 American Chemical Society. CODEN: JOCEAH.Chemicals with cas numbers 918963-32-3 and 148-53-8 also play role. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 24 (Alicyclic Compounds) Section cross-reference(s): 78 Isophorone diamine [IPDA, 3-(aminomethyl)-3,5,5-trimethylcyclohexylamine] is a chiral non-C2-sym. 1,4-diamine which is produced industrially on large scale as the mixt. of all four stereoisomers (cis/trans ca. 3:1). Starting from this industrial bulk product, the prepn. of the bis-tosyl, bis-Fmoc, bis-Boc and bis-Cbz derivs. of cis-IPDA, the prepn. of the pure cis enantiomers by HPLC on chiral stationary phase, and the assignment of abs. configurations to the isolated enantiomers are described. Furthermore, an efficient method for the optical resoln. of IPDA by salt formation with dibenzoyl tartaric acid, which conveniently affords enantiomerically pure cis-IPDA in 100 g quantities, is reported. A no. of salen ligands have been prepd. from this enantiomerically pure 1,4-diamine and fully characterized. The nickel complex of one of the salen ligands was prepd. and analyzed by X-ray crystallog. The crystal structure of the Ni4L4 complex illustrates the pronounced preference of cis-IPDA for adopting the chair conformation in which both the amino- and the aminomethyl substituents occupy equatorial positions. As a consequence, the two salicylidene imine moieties of one ligand mol. do not converge on one metal ion, but act as bridging ligands between two nickel ions. .