69527-02-2Relevant academic research and scientific papers
Two novel flexible multidentate ligands for crystal engineering: Syntheses, structures, and properties of CuII, MnII complexes with N-[(3-carboxyphenyl)-sulfonyl]glycine and N,N′-(1,3-phenylenedisulfonyl) bis(glycine)
Ma, Lu-Fang,Wang, Yao-Yu,Wang, Li-Ya,Liu, Jian-Qiang,Wu, Ya-Pan,Wang, Jian-Ge,Shi, Qi-Zhen,Peng, Shie-Ming
, p. 693 - 703 (2008)
One novel N-[(3-carboxyphenyl)sulfonyl]glycine (H3L1) ligand (1) was prepared in high yield, and its structure was determined by single-crystal X-ray diffraction. Reaction of H3L1 with Mn(ClO4)2·6H2O at different pH values gave two new dinuclear complexes: [Mn2(HL1) 2(phen)4]·16H2O (2) and [Mn 2L1(phen)4(H2O)]ClO 4·3H2O (3) (phen = 1,10-phenanthroline). Additionally, two copper(II) complexes, [K2Cu(L2) 2-(H2O)2]n (4) and [CuL 2(H2O)]2·2H2O (5), involving another novel ligand, N,N′-(1,3-phenylenedisulfonyl)bis(glycine) (H 2L2), were prepared by a one-pot reaction of 1,3-phenylenebis(sulfonyl chloride), glycine, and KOH or triethylamine in the presence of CuII ions. A self-assembled (H2O)30 cluster containing a puckered (H2O)12 ring core was found in 2, which presents a new mode of association of water molecules not predicted theoretically or previously observed experimentally. Furthermore, 2 forms a 2-D supramolecular structure through hydrogen bonding and unique π-π stacking interactions. In 3, there also exist discrete trimeric water clusters. The identity of the base determines the specific structural characteristics of 4 and 5. When potassium hydroxide was used for the synthesis of 4, it led to a 3-D copper(II)-potassium(I) coordination polymer; when triethylamine was used, paddle-wheel dinuclear units of copper(II) carboxylate were produced. Magnetic measurements show that there are weak antiferromagnetic interactions in 2-4. In 5 the χMT vs. T curve shows a minimum at 110 K and a climb from 110 K to 5 K, then a long-range antiferromagnetic ordering occurs, as revealed by a decrease in χMT with T. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Protease inhibitors - Part 5. Alkyl/arylsulfonyl- and arylsulfonylureido-/arylureido- glycine hydroxamate inhibitors of Clostridium histolyticum collagenase
Scozzafava, Andrea,Supuran, Claudiu T.
, p. 299 - 307 (2007/10/03)
Reaction of alkyl/arylsulfonyl halides with glycine afforded a series of derivatives which were first N-benzylated by treatment with benzyl chloride, and then converted to the corresponding hydroxamic acids with hydroxylamine in the presence of carbodiimide derivatives. Other derivatives were obtained by reaction of N-benzyl-glycine with aryl isocyanates, arylsulfonyl isocyanates or benzoyl isothiocyanate, followed by conversion of their COOH group into the CONHOH moiety, as mentioned above. The 90 new compounds reported here were assayed as inhibitors of the Clostridium histolyticum collagenase (EC 3.4.24.3), a zinc enzyme which degrades triple helical regions of native collagen. The prepared hydroxamate derivatives were generally 100-500 times more active than the corresponding carboxylates. In the series of synthesized hydroxamates, substitution patterns leading to the best inhibitors were those involving perfluoroalkylsulfonyl- and substituted- arylsulfonyl moieties, such as pentafluorophenylsulfonyl, 3- and 4- carboxyphenylsulfonyl-, 3-trifluoromethyl-phenylsulfonyl or 1- and 2-naphthyl among others. Thus, it seems that similarly to the matrix metalloproteinase (MMP) hydroxamate inhibitors, Clostridium histolyticum collagenase inhibitors should incorporate hydrophobic moieties at the P1, and P2, sites, whereas the α-carbon substituent may be a small and compact moiety (such as H. for the Gly derivatives reported here). Such compounds might lead to the design of collagenase inhibitor-based drugs useful as anti-cancer, anti-arthritis or anti-bacterial agents for the treatment of corneal keratitis. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
