Structures of histamine H<sub>1</sub>-receptor antagonists derived from the cimetidine group of histamine H<sub>2</sub>-receptor antagonists

Bannister, C.; Burns, K.; Prout, Keith; Watkin, David J.; Cooper, D. G.; Durant, G. J.; Ganellin, C. Robin; Ife, Robert J.; Sach, G. S.

doi:10.1107/s0108768193010407

Cited by 5 publications

(2 citation statements)

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“…In the structures of halogenated organic salts, discrete adducts are more common than infinite nets, probably not due to an inherent preference of anions to work as monodentate XB acceptors but, rather, due to the fact that monohalogenated organic cations are much more numerous than di- or polyhalogenated ones. In monohalopyridinium halides − and monohaloanilinium halides − the monodentate cation prevents the anion from functioning as a polydentate unit, and discrete adducts are formed (Figure , LEJKUG, WUWMAD, WOQREB, VOQMUJ, CICRAI, HOLLID, and ZONXOP).…”

Section: Crystal Engineeringmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Crystal Engineeringmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…In compound 1, [ZnCl 3 LH], the zinc ion adopts a distorted tetrahedral geometry with a {3Cl, 1O} donor set involving the Table 1 Selected bond lengths (Å) and angles (Њ) for compounds 1-3 4) C( 4)᎐O( 4) C( 4)᎐C( 5) C( 5)᎐C( 6) C( 6)᎐N( 1) M᎐O( 4) M᎐N( 2) M᎐N( 3) M᎐N( 12) M᎐Cl( 1) M᎐Cl( 2) M᎐Cl( 3) M᎐O( 1) C( 2)᎐N( 3)᎐C( 4 A few structural reports have been made on alkylaminopyrimidines, though to the best of our knowledge none of their metal complexes. 12 The carbonyl bond lengths in 2-(5-bromo-3methyl-2-pyridyl)butylaminopyrimid-4-one, 13 1-methylcytosine 14 and isocytosine 15 are 1.249, 1.234 and 1.248 Å, respect- If comparison with nucleobases is to be made it is most appropriate for cytosine, as here both a carbonyl and amino function are present, although these are in the 2-and 4-positions, respectively. Crystallographically characterized Zn II complexes of cytosine reveal that N 3 is a general binding site, 17,18 though in the trinuclear [Zn 3 (OH) 2 (1-MeCyt) 8 ][NO 3 ] 4 either of N 3 or O 2 acts as donor atom.…”

Section: Crystal and Molecular Structures Of 1 2 Andmentioning

confidence: 99%

Mono-, di- and tri-dentate binding modes of a substituted isocytosine derivative in complexes of palladium and zinc

Price¹,

Rees²,

Elsegood³

et al. 1998

J. Chem. Soc., Dalton Trans.

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Synthesis, Characterization, and Thermal Behavior of Polydentate Ligand Adducts of Barium Trifluoroacetate

1998

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The reaction of BaH 2 with polydentate ligands and CF 3 COOH in THF at -40 °C in 1:1:2 stoichiometries leads to compounds of general formula [Ba(O 2 CCF 3 ) 2 ] m L n (L ) 12-crown-4 (1), triglyme (2), 2-(hydroxymethyl)-15crown-5 (15-crown-5CH 2 OH) (3), cryptand(222) (4), 18-crown-6‚C 5 H 5 N (5), 2-(hydroxymethyl)-18-crown-6 (18crown-6CH 2 OH) (6)). A sulfonate compound, Ba(O 3 SCF 3 ) 2 (tetraglyme) (7), was also prepared by a similar reaction. The polydentate ligands of 1-6 are coordinated to the barium atoms through all of their donating atoms, and the trifluoroacetate ligands are found in four distinct types of bonding modes. The compounds were characterized by spectroscopic and analytical methods, and 1-6 are among the first examples of group 2 trifluoroacetate compounds with mononuclear or dinuclear structures in the solid state as determined by single-crystal X-ray diffraction. Ba 2 (O 2 CCF 3 ) 4 (12-crown-4) 2 (1) crystallizes from ethanol in monoclinic space group P2 1 /n with a ) 11.014(1) Å, b ) 12.016(1) Å, c ) 15.269(1) Å, β ) 104.47(1)°, and Z ) 4. Ba 2 (O 2 CCF 3 ) 4 (triglyme) 2 (2) crystallizes from ethanol in monoclinic space group P2 1 /n with a ) 11.203(1) Å, b ) 12.220(1) Å, c ) 15.451(1) Å, β ) 107.61(1)°, and Z ) 4. Ba 2 (O 2 CCF 3 ) 4 (15-crown-5CH 2 OH) 2 (3) crystallizes from ethanol in monoclinic space group P2 1 /c with a ) 12.445(2) Å, b ) 12.499(3) Å, c ) 15.615(2) Å, β ) 111.11 (1)°, and Z ) 4. Ba(O 2 CCF 3 ) 2 (cryptand( 222)) ( 4) crystallizes from toluene in the tetragonal space group P4 3 2 1 2 with a ) b ) 9.263(2) Å, c ) 35.897(7) Å, and Z ) 4. Ba(O 2 CCF 3 ) 2 (18-crown-6)(py) (5) crystallizes from pyridine in orthorhombic space group Pnma with a ) 27.178(3) Å, b ) 11.417(1) Å, c ) 9.133(1) Å, and Z ) 4. Ba(O 2 -CCF 3 ) 2 (18-crown-6CH 2 OH) (6) crystallizes from ethanol in monoclinic space group Pn with a ) 8.279(1) Å, b ) 11.410(1) Å, c ) 13.661(2) Å, β ) 98.41(1)°, and Z ) 2. Infrared spectroscopy on 1-6 supplied information on the relationships among ν asym (CO 2 ), bonding mode of the trifluoroacetate ligand, and donating ability of the polydentate ligand. Thermogravimetric analysis of 1-7 shows loss of the organic supporting ligands in the temperature range 250-600 °C with formation of BaF 2 .

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Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists

Cited by 5 publications

References 14 publications

The Halogen Bond

The Halogen Bond

Mono-, di- and tri-dentate binding modes of a substituted isocytosine derivative in complexes of palladium and zinc

Synthesis, Characterization, and Thermal Behavior of Polydentate Ligand Adducts of Barium Trifluoroacetate

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Structures of histamine H1-receptor antagonists derived from the cimetidine group of histamine H2-receptor antagonists

Cited by 5 publications

References 14 publications

The Halogen Bond

The Halogen Bond

Mono-, di- and tri-dentate binding modes of a substituted isocytosine derivative in complexes of palladium and zinc

Synthesis, Characterization, and Thermal Behavior of Polydentate Ligand Adducts of Barium Trifluoroacetate

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Product

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Structures of histamine H₁-receptor antagonists derived from the cimetidine group of histamine H₂-receptor antagonists