Dichloro(2,2′-diamino-4,4′-bi-1,3-thiazole-N3,N3′)copper(II)

Liu, Jiageng; Nie, Jun; Xü, Dong; Xu, Yiming; Wu, Jing‐Yun; Chiang, Michael Y.

doi:10.1107/s0108270100020163

Cited by 4 publications

(7 citation statements)

References 6 publications

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“…A N–H···N hydrogen-bonded 2D herringbone layer has been confirmed in the single crystal X-ray structural analysis of 1 (Figure a). , The packing structure is almost maintained in crystalline powders 1 ·(Py) 2 following the adsorption of two molar Py (Figure b). The 2D herringbone layer of 1 is constructed by the intermolecular N–H···N hydrogen-bonding interactions between its −NH 2 group and the ring nitrogen atom.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Molecule 1 was soluble in many common organic solvents, forming various types of host–guest molecular crystals. The crystal structure of 1 indicated the presence of intermolecular N–H···N hydrogen-bonding and S···N interactions, which formed a 2D herringbone packing structure with an orthogonal molecular arrangement. , Since the π-electronic structure of 1 is essentially inert for redox reactions, the magnetic properties of metal (Cu and Fe)-ligand coordination complexes involving 1 have been examined. , However, formation of host–guest molecular crystals involving 1 , which is capable of forming hydrogen bonds, and their associated molecular adsorption–desorption properties have not yet been examined. To this end, the host–guest molecular crystals 1 with benzonitrile (PhCN), pyridine (Py), 1,4-dioxane (Diox), DMF, THF, and CH 3 OH were successfully obtained, showing reversible molecular desorption–adsorption following crystal heating and guest vapor exposure.…”

Section: Introductionmentioning

confidence: 99%

“…The crystal structure of 1 indicated the presence of intermolecular N−H•••N hydrogen-bonding and S•••N interactions, which formed a 2D herringbone packing structure with an orthogonal molecular arrangement. 86,87 Since the π-electronic structure of 1 is essentially inert for redox reactions, the magnetic properties of metal (Cu and Fe)-ligand coordination complexes involving 1 have been examined. 86,87 However, formation of host−guest molecular crystals involving 1, which is capable of forming hydrogen bonds, and their associated molecular adsorption−desorption properties have not yet been examined.…”

Section: ■ Introductionmentioning

confidence: 99%

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Host–Guest Molecular Crystals of Diamino-4,4-bithiazole and Dynamic Molecular Motions via Guest Sorption

Nishiyama

Takeda

Hoshino

et al. 2017

Crystal Growth & Design

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Diamino-4,4-bithiazole (1) formed host–guest binary molecular crystals with various types of organic guest molecules including pyridine (Py), benzonitrile (PhCN), piperidine (Pipe), DMF, THF, 1,4-dioxane (Diox), CH3OH, aniline (Ani), coumarin (Coum), nitrobenzene (PhNO2), hexamethylenetetramine (HMTA), and quinoline (Quino). Single crystal X-ray structural analyses at 100 K revealed the formation of 1·(guest) or 1·(guest)2 crystals. Reversible molecular adsorption–desorption responses were observed with Py, PhCN, Pipe, DMF, and Diox around room temperature as the crystalline powders were heated during the desorption process and exposed to guest vapor during the readsorption process. The adsorption–desorption isotherms of crystalline powders 1 with Diox at 298 K indicated a reversible gate-opening adsorption–desorption process. Although the host–guest molecular crystals 1·(THF)2 and 1·(CH3OH)2 were confirmed by X-ray crystal structural analyses at 100 K, the THF and CH3OH guests were already eliminated at room temperature. Guest desorption processes of crystalline powders 1·(guest) x were not observed in the host–guest molecular crystals with Ani, Coum, PhNO2, HMTA, and Quino after the crystalline powders were heated. A balance of both the dipole moment and vapor pressure of the guest molecules played an essential role to elicit reversible guest sorption. The crystal structures formed on account of double N–H···N hydrogen-bonded one-dimensional (1D) chains between the −NH2 group and the ring nitrogen atom of 1, which interacted to form two-dimensional (2D) sheet structures through π-stacking and/or S···S interactions. Alternating layers of N–H···N hydrogen-bonded herringbone packing of 1 and the guest molecules led to the formation of other types of crystal lattices. The hydrogen-bonding molecular assemblies of 1 demonstrated lattice flexibly via the configuration change in the molecular arrangements according to the boiling point of the guest molecules.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Host–Guest Molecular Crystals of Diamino-4,4-bithiazole and Dynamic Molecular Motions via Guest Sorption

Nishiyama

Takeda

Hoshino

et al. 2017

Crystal Growth & Design

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“…1 and Table IV. DABT chelates to the Mn(II) atom with a coplanar configuration, the maximum atomic deviation being 0.052(2) Å [C(5 0 )]. This is different from the twisted structures of thiazole found in a Cd(II) complex [6] and an Ni(II) complex [7], but comparable to that found in a Cu(II) complex [8]. [9].…”

Section: Crystal Structurementioning

confidence: 94%

Synthesis and crystal structure of aqua (2,2′-diamino-4,4′-bi-1,3-thiazole) (oxydiacetato)manganese(II) trihydrate

Luo

Xü

et al. 2004

Journal of Coordination Chemistry

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The title compound crystallizes in the triclinic space group P 1 1 with a ¼ 7.194(3), b ¼ 9.790(5), c ¼ 12.492(1) Å , ¼ 82.407(16), ¼ 86.664(15), ¼ 89.882(15) . The Mn(II) complex assumes distorted octahedral coordination geometry, formed by diaminobithiazole (DABT), an oxydiacetate dianion (ODA) and a water molecule. The tridentate ODA ion chelates to the Mn(II) atom in a meridional configuration. Each carboxyl group coordinates to the Mn(II) atom as a monodentate. Uncoordinated carboxyl oxygen atoms are involved in a hydrogen-bonding network. DABT chelates to the Mn(II) atom with a coplanar configuration. Coordinated water is hydrogen bonded to carboxyl groups of ODA of a neighboring complex to form supramolecular chains. A -stacking interaction involving thiazole rings occurs between adjacent supramolecular chains. A difference of 180 cm À1 between asymmetric and symmetric stretching vibrations of the carboxyl group corresponds to the extensive hydrogen-bonding network involving the carboxyl group.

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“…Xu and coworkers recently reported the synthesis and the structure of 1 : 1 Cu(II)-complex of 2,2Ј-diamino-4,4Ј-bithiazole. 25) Yang and coworkers also indicated the formation and the structural features of 2 : 1 Co(II)-complex of 2,2Ј-diamino-4,4Ј-bithiazole. 26,27) The formation of 3 : 1 complexes of 4,4Ј-bithiazole with iron and nickel were demonstrated by Baker and Goodwin.…”

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confidence: 99%

Synthesis of 2,2'-Bis(3,6,9-triazanonyl)-4,4'-bithiazole and Related Compounds as New DNA Cleavage Agents

Sasaki

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Recently, the synthesis and properties of many metal complexes of amines and cyclic amines used as DNA cleavage agents have been reported. [1][2][3][4] These compounds generally contain heterocycles or polycyclic aromatic rings tethered to one or more aminoalkyl side chains, and are complexed with transition metals known to play important roles in DNA cleavage reactions. Many studies on the role of 2,4Ј-bithiazole, which constitutes a part of the C-terminus of Bleomycin, a naturally occurring anticancer agent, have also been reported. 5-7) Previously, we reported the synthesis and metal-dependent DNA cleavage activities of 4,4Ј-bithiazoles (1a, b) linked to two aminoalkyl groups at the side chain, [8][9][10] since the synthesis of substituted 4,4Ј-bithiazoles is simpler than the synthesis of 2,4Ј-bithiazoles. Our studies on these 4,4Ј-bithiazole derivatives demonstrated that 2,2Ј-bis(2-aminoethyl)-4,4Ј-bithiazole (1b) could cleave DNA under physiological conditions only in the presence of Co(II), and that DNA cleavage efficiently progressed in the absence of reductants, oxygen and light.9) It was also found that DNA cleavage by 2,2Ј-bis(aminomethyl)-4,4Ј-bithiazole (1a) required Cu(II) ions whereas 2,2Ј-bis(3-aminopropyl)-4,4Ј-bithiazole (1c) could not cleave DNA in the presence of any metal. 8,9) We also showed that 2,2Ј-bis(3,6-diazahexyl)-and 2,2Ј-bis(3,7-diazaheptyl)-4,4Ј-bithiazoles (2a, b) with additional aminoalkyl groups substituted on the amino group of each side chain of 1b did not initiate detectable DNA cleavage in the presence of Co(II) at pH 7.0 after half an hour of incubation.11) These results showed that the structure of the aminoalkyl side chains of the 4,4Ј-bithiazles determined the metal selectivity and DNA cleavage activities of these bithiazoles (1, 2). However, Stewart demonstrated that naturally occurred polyamines such as spermine, spermidine, putrescine and their derivatives strongly bind double-stranded DNA.12) Moreover, several authors have reported that many compound containing polyaminoalkyl moieties, such as spermine, spermidine and ethylenediamine, interact efficiently with DNA. 13,14) These studies prompted us to synthesize new 4,4Ј-bihiazoles substituted with polyaminoalkyl groups at each side chain, and to expect that these new compounds would interact efficiently with DNA and exhibit enhanced DNA cleavage activity. We report herein the synthesis, affinities for double-stranded DNA, and plasmid DNA cleavage abilities of new 4,4Ј-bithiazole derivatives (3). These new compounds possess longer side chains, such as 3,6,9-triazanonyl-and 3,7,11-triazaundecyl groups, than those of 1 and 2, as shown in Fig. 1. Furthermore, bithiazole derivatives (4), used as reference compounds for 3a were prepared by acylating the amino groups of 1b and 2a with amino acids. This derivatization was conducted in order to elucidate the role of the amino groups at the 3-and 6-positions of the side chains of 3a in binding to and cleaving double-stranded DNA. The structural features of the 4,4Ј-bithiazole ...

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Dichloro(2,2′-diamino-4,4′-bi-1,3-thiazole-N³,N^3′)copper(II)

Cited by 4 publications

References 6 publications

Host–Guest Molecular Crystals of Diamino-4,4-bithiazole and Dynamic Molecular Motions via Guest Sorption

Host–Guest Molecular Crystals of Diamino-4,4-bithiazole and Dynamic Molecular Motions via Guest Sorption

Synthesis and crystal structure of aqua (2,2′-diamino-4,4′-bi-1,3-thiazole) (oxydiacetato)manganese(II) trihydrate

Synthesis of 2,2'-Bis(3,6,9-triazanonyl)-4,4'-bithiazole and Related Compounds as New DNA Cleavage Agents

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