132551

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Unique properties of DNA interstrand cross-links of antitumor oxaliplatin and the effect of chirality of the carrier ligand.

Jana Kasparkova et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 14(4), 1330-1341 (2007-11-21)

The different antitumor and other biological effects of the third-generation antitumor platinum drug oxaliplatin [(1R,2R-diamminocyclohexane)oxalatoplatinum(II)] in comparison with those of conventional cisplatin [cis-diamminedichloridoplatinum(II)] are often explained by the ability of oxaliplatin to form DNA adducts of different conformation and consequently

The in vitro antitumour profile of some 1,2-diaminocyclohexane organotin complexes.

J J Bonire et al.

Journal of inorganic biochemistry, 83(2-3), 217-221 (2001-03-10)

Platinum compounds containing the ligand 1,2-diaminocyclohexane (DACH) such as tetraplatin [PtCl4(DACH)] have been found to be active in cisplatin-resistant tumour models. In an attempt to develop novel metal-based drugs with a different therapeutic profile to cisplatin, we have synthesised a

Critical role of external axial ligands in chirality amplification of trans-cyclohexane-1,2-diamine in salen complexes.

Takuya Kurahashi et al.

Journal of the American Chemical Society, 131(34), 12394-12405 (2009-08-27)

A series of Mn(IV)(salen)(L)(2) complexes bearing different external axial ligands (L = Cl, NO(3), N(3), and OCH(2)CF(3)) from chiral salen ligands with trans-cyclohexane-1,2-diamine as a chiral scaffold are synthesized, to gain insight into conformational properties of metal salen complexes. X-ray

Quantification of trace elements in natural samples by electrospray ionization mass spectrometry with a size-exclusion column based on the formation of metal-aminopolycarboxylate complexes.

Hiroki Hotta et al.

Analytical chemistry, 81(15), 6357-6363 (2010-03-27)

Metal ions were determined by ESI-MS in the negative ion mode as monovalent negative ions of their aminopolycarboxylic acid (APC) complexes, e.g., [Al(cydta)](-), [Pb(Hcydta)](-), where excess amounts of the APC agents were added to sample solutions. Among several APCs studied

Simple cyclohexanediamine-derived primary amine thiourea catalyzed highly enantioselective conjugate addition of nitroalkanes to enones.

Kui Mei et al.

Organic letters, 11(13), 2864-2867 (2009-06-03)

A highly enantioselective conjugate addition of nitroalkanes to enones has been developed. The process is efficiently catalyzed by a simple chiral cyclohexanediamine-derived primary amine thiourea with a broad substrate scope.

(3+ 3)-Cyclocondensation of the enantiopure and racemic forms of trans-1, 2-diaminocyclohexane with terephthaldehyde. Formation of diastereomeric molecular triangles and their stereoselective solid-state stacking into microporous chiral columns.

Chadim M, et al.

Tetrahedron Asymmetry, 12(1), 127-133 (2001)

Chiral diaminopyrrolic receptors for selective recognition of mannosides, part 1: design, synthesis, and affinities of second-generation tripodal receptors.

Cristina Nativi et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 17(17), 4814-4820 (2011-03-10)

A new generation of chiral tripodal receptors for recognition of carbohydrates, featuring trans-1,2-diaminocyclohexane as a key structural element, and their recognition properties toward a set of glycosides of biologically relevant monosaccharides is described. The introduction of a chelating diamino unit

Interactions of an asymmetric amine with a non-C2 symmetric Cu-salen complex: an EPR/ENDOR and HYSCORE investigation.

Ignacio Caretti et al.

Physical chemistry chemical physics : PCCP, 13(45), 20427-20434 (2011-10-14)

Single enantiomers of R-/S-methylbenzylamine (MBA) were found to selectively form adducts with the chiral non-C(2) symmetric Cu-salen complex N-(3,5-di-tert-butylsalicylidene)-N'-(salicylidene)-cyclohexane-1,2-diamine copper(II), hereafter labelled [Cu(3)]. The g/A spin Hamiltonian parameters of this Cu(II) complex showed a decrease in symmetry from axial to

Synthesis, spectroscopic, structural characterization, electrochemical and antimicrobial activity studies of the Schiff base ligand and its transition metal complexes.

Mehmet Aslantaş et al.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 74(3), 617-624 (2009-08-04)

In this study, the Schiff base ligand trans-N,N'-bis[(2,4-dichlorophenyl) methylidene] cyclohexane-1,2-diamine (L) and its copper(II), nickel(II) and palladium(II) transition metal complexes were prepared and characterized by the analytical and spectroscopic methods. The (1)H((13)C) NMR spectra of the ligand and its diamagnetic

Porous organic cage crystals: characterising the porous crystal surface.

Michael J Bojdys et al.

Chemical communications (Cambridge, England), 48(98), 11948-11950 (2012-11-06)

The characterisation of porous crystalline solids often relies on single crystal X-ray diffraction, which does not give direct information about the surface of the material. Here, crystals of a porous organic cage, CC3-R, are investigated by atomic force microscopy and

Stereoselective UV sensing of 1,2-diaminocyclohexane isomers based on ligand displacement with a diacridylnaphthalene N,N'-dioxide scandium complex.

Daniel P Iwaniuk et al.

The Journal of organic chemistry, 77(11), 5203-5208 (2012-05-12)

Stereoselective displacement of diacridylnaphthalene N,N'-dioxide ligands, 1, from a scandium(III) complex can be used for quantitative detection of 1,2-diaminocyclohexane isomers. The diastereoselective sensing assay with Sc(syn-1)(2) shows excellent linearity between the sample de and the measured UV absorption change, and

Anion-induced self-assembly of luminescent and magnetic homoleptic cyclic tetranuclear Ln4(salen)4 and Ln4(salen)2 complexes (Ln = Nd, Yb, Er, or Gd).

Weixu Feng et al.

Inorganic chemistry, 51(21), 11377-11386 (2012-10-10)

Unique homoleptic cyclic tetranuclear Ln(4)(Salen)(4) complexes [Ln(4)(L)(2)(HL)(2)(μ(3)-OH)(2)Cl(2)]·2Cl (Ln = Nd, 1; Ln = Yb, 2; Ln = Er, 3; Ln = Gd, 4) or Ln(4)(Salen)(2) complexes [Ln(4)(L)(2)(μ(3)-OH)(2)(OAc)(6)] (Ln = Nd, 5; Ln = Yb, 6; Ln = Er, 7; Ln

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: exploration of 5-6 fused rings as alternative S1 moieties.

Kenji Yoshikawa et al.

Bioorganic & medicinal chemistry, 17(24), 8206-8220 (2009-11-04)

A series of cis-1,2-diaminocyclohexane derivatives were synthesized with the aim of optimizing previously disclosed factor Xa (fXa) inhibitors. The exploration of 5-6 fused rings as alternative S1 moieties resulted in two compounds which demonstrated improved solubility and reduced food effect

trans-1,2-Diaminocyclohexane mesoporous silica for asymmetric catalysis: enhancement of chirality through confinement space by the plug effect.

Eun-Young Jeong et al.

Chemical communications (Cambridge, England), 48(25), 3079-3081 (2012-02-22)

trans-1,2-Diaminocyclohexane functionalized mesoporous silica was applied as an ideal catalyst for asymmetric Michael addition of various nitroalkane derivatives. Short channels and plugs in the pore structure offered chiral enhancement in Michael addition.

Chiral ruthenium (IV)-oxo complexes. Structure, reactivities of [Ru (terpy)(Nn N) O]²⁺Nn N= N, N, N', N'-tetramethyl-1, 2-diaminocyclohexane) and [Ru (Me₃tacn)(cbpy) O]²⁺(cbpy=(-)-3, 3'-[(4 S-trans)-1, 3-dioxolane-4, 5-dimethyl]-2, 2'-bipyridine).

Cheng WC, et al.

Inorgorganica Chimica Acta, 242(1), 105-113 (1996)

A mechanistic approach for the DNA binding of chiral enantiomeric L- and D-tryptophan-derived metal complexes of 1,2-DACH: cleavage and antitumor activity.

Farukh Arjmand et al.

Chirality, 23(3), 250-259 (2010-10-12)

A new chiral series of potential antitumor metal-based complexes 1-3(a and b) of L- and D-tryptophan have been synthesized and thoroughly characterized. Both enantiomers of 1-3 bind DNA noncovalently via phosphate interaction with slight preference of metal center for covalent

Synthesis, in vitro cytotoxicity, and interaction with DNA of platinum(II) complexes with N-monocycloalkyl derivatives of 1R,2R-diaminocyclohexane as carrier ligands.

Yanyan Sun et al.

ChemMedChem, 7(4), 642-649 (2012-01-17)

A series of platinum(II) complexes with N-monocyclopentyl/cyclohexyl derivatives of 1R,2R-diaminocyclohexane as carrier ligands and dicarboxylate anions as leaving groups were synthesized and characterized. All complexes were characterized by elemental analysis, IR, (1)H NMR, and (13)C NMR spectroscopy, as well as

Helix-forming propensity of aliphatic urea oligomers incorporating noncanonical residue substitution patterns.

Nagendar Pendem et al.

Journal of the American Chemical Society, 135(12), 4884-4892 (2013-03-01)

Aliphatic N,N'-linked oligoureas are peptidomimetic foldamers that adopt a well-defined helical secondary structure stabilized by a collection of remote three-center H-bonds closing 12- and 14-membered pseudorings. Delineating the rules that govern helix formation depending on the nature of constituent units

Oligopyrenotides: abiotic, polyanionic oligomers with nucleic acid-like structural properties.

Robert Häner et al.

Journal of the American Chemical Society, 132(21), 7466-7471 (2010-05-13)

Oligopyrenotides, abiotic oligomers that exhibit significant structural analogies to the nucleic acids, are described. They are composed of achiral, phosphodiester-linked pyrene building blocks and a single chiral 1,2-diaminocyclohexane unit. These oligomers form stable hybrids in aqueous solution. Hybridization is based

Antitumor platinum(II) complexes of N-monoalkyl-1R, 2R-diaminocyclohexane derivatives with alkyl groups as hindrance.

Yanyan Sun et al.

Journal of inorganic biochemistry, 112, 68-76 (2012-05-09)

A number of platinum (II) complexes, characteristic of (1R,2R)-N(1)-alkyl-1,2-diaminocyclohexane derivatives as carrier ligands, were designed, synthesized and characterized, where the alkyl group serving as hindrance is a 1-butyl, 2-methylpropyl or 2-butyl moiety, respectively. In vitro biological evaluation of these platinum

A new "fully reduced" polyoxovanadate constructed from nanosized triangle-shaped [V(III)3V(IV)18P6O60(DACH)3]}9- cluster anions exhibiting ferrimagnetic interactions.

Cong-Ling Wang et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 18(38), 11909-11912 (2012-08-15)

Magnetic personality: A pentavalent vanadium source was employed to prepare the largest highly reduced polyoxovanadate cluster by virtue of the reducing power of 1,2-diaminocyclohexane under hydrothermal conditions. The new non-classical triangle-shaped cluster shows good catalytic selectivity for the oxidation of

Steric modifications tune the regioselectivity of the alkane oxidation catalyzed by non-heme iron complexes.

Yu He et al.

Inorganic chemistry, 50(24), 12651-12660 (2011-11-11)

Iron complexes with the tetradentate N-donor ligand N,N'-di(phenylmethyl)-N,N'-bis(2-pyridinylmethyl)-1,2-cyclohexanediamine (bbpc) are reported. Despite the benzyl groups present on the amines, the iron compounds catalyze the oxygenation of cyclohexane to an extent similar to those employing less sterically encumbered ligands. The catalytic

Origins of enantioselectivity in asymmetric ketone hydrogenation catalyzed by a RuH2(binap)(cydn) complex: insights from a computational study.

Ran Feng et al.

Dalton transactions (Cambridge, England : 2003), 42(6), 2130-2145 (2012-11-29)

In this paper, the origins of enantioselectivity in asymmetric ketone hydrogenation catalyzed by RuH(2)(binap)(cydn) (cydn = trans-1,2-diaminocyclohexane) were discussed. Fifteen substrates involving aromatic, heteroaromatic, olefinic and dialkyl prochiral ketones were used to probe the catalytic mechanism and find an effective

Trans-cyclohexanediamines prevent thermal inactivation of protein: role of hydrophobic and electrostatic interactions.

Atsushi Hirano et al.

The protein journal, 27(4), 253-257 (2008-02-27)

Although solution additives prevent protein misfolding, the mechanism remains elusive. In this paper, we compare the preventive effects of trans-1,2-cyclohexanediamine (1,2-CHDA) and trans-1,4-cyclohexanediamine (1,4-CHDA) on the heat-induced inactivation of ribonuclease A (RNase A) and lysozyme. These additives are more effective

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part II: exploration of 6-6 fused rings as alternative S1 moieties.

Kenji Yoshikawa et al.

Bioorganic & medicinal chemistry, 17(24), 8221-8233 (2009-11-11)

A series of cis-1,2-diaminocyclohexane derivatives possessing a 6-6 fused ring for the S1 moiety were synthesized as novel factor Xa (fXa) inhibitors. The synthesis, structure-activity relationship (SAR), and physicochemical properties are reported herein, together with the discovery of compound 45c

Design, synthesis, and biological evaluation of pirenzepine analogs bearing a 1,2-cyclohexanediamine and perhydroquinoxaline units in exchange for the piperazine ring as antimuscarinics.

Anna Minarini et al.

Bioorganic & medicinal chemistry, 16(15), 7311-7320 (2008-07-04)

Pirenzepine (2) is one of the most selective muscarinic M(1) versus M(2) receptor antagonists known. A series of 2 analogs, in which the piperazyl moiety was replaced by a cis- and trans-cyclohexane-1,2-diamine (3-6) or a trans- and cis-perhydroquinoxaline rings (7

Diastereoselective imine-bond formation through complementary double-helix formation.

Hidekazu Yamada et al.

Journal of the American Chemical Society, 134(17), 7250-7253 (2012-04-18)

Optically active amidine dimer strands having a variety of chiral and achiral linkers with different stereostructures are synthesized and used as templates for diastereoselective imine-bond formations between two achiral carboxylic acid monomers bearing a terminal aldehyde group and racemic 1,2-cyclohexanediamine

Mechanical stimulation of human tendon stem/progenitor cells results in upregulation of matrix proteins, integrins and MMPs, and activation of p38 and ERK1/2 kinases.

Cvetan Popov et al.

BMC molecular biology, 16, 6-6 (2015-04-17)

Tendons are dense connective tissues subjected periodically to mechanical stress upon which complex responsive mechanisms are activated. These mechanisms affect not only the development of these tissues but also their healing. Despite of the acknowledged importance of the mechanical stress

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