Conformational preferences in model antiviral compounds: A spectroscopic and computational study of phenylurea and 1,3-diphenylurea

被引：24

作者：

Emery, R ^{[1
]}

Macleod, NA ^{[1
]}

Snoek, LC ^{[1
]}

Simons, JP ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Phys & Theoret Chem Lab, Oxford OX1 3QZ, England

来源：

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | 2004年 / 6卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1039/b400390j

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The conformational preferences of two model anti-viral pharmaceuticals, phenylurea and 1,3-diphenylurea, isolated in the gas phase, have been explored using a combination of ultra-violet and infra-red ion-dip spectroscopy and quantum chemical computation. Two conformers have been assigned for each species associated with cis and trans configurations of the amide groups and stabilised by weak intramolecular hydrogen bonding between the amide group and the aromatic ring, NH --> pi (cis) or CH --> O=C (trails). In 1,3-diphenyl urea, the folded (global minimum) trans-cis and the extended trans trans conformers were both populated but the highly folded cis-cis structure, located at considerably higher energy, could not be detected.

引用

页码：2816 / 2820

页数：5

共 27 条

[1] Molecular cocrystals of aromatic carboxylic acids with unsymmetrically substituted ureas.: The structures of phenylurea and the 1:1 adducts of phenylurea with a series of nitro-substituted acids [J].

Bott, RC ;

Smith, G ;

Wermuth, UD ;

Dwyer, NC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (09) :767-777

[2] Free jet rotational spectrum and ab initio calculations of acetanilide [J].

Caminati, W ;

Maris, A ;

Millemaggi, A .

NEW JOURNAL OF CHEMISTRY, 2000, 24 (10) :821-824

[3] Nonsymmetric P2/P2′ cyclic urea HIV protease inhibitors.: Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues [J].

De Lucca, GV ;

Kim, UT ;

Liang, J ;

Cordova, B ;

Klabe, RM ;

Garber, S ;

Bacheler, LT ;

Lam, GN ;

Wright, MR ;

Logue, KA ;

Erickson-Viitanen, S ;

Ko, SS ;

Trainor, GL .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (13) :2411-2423

[4] CRYSTALLOGRAPHIC DATA ON DISUBSTITUTED SYMMETRIC UREAS [J].

DESHAPANDE, SV ;

MEREDITH, CC ;

PASTERNAK, RA .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1968, B 24 :1396-+

[5] Molecular and supramolecular structures of N-phenyl formamide and its hydrated clusters [J].

Dickinson, JA ;

Hockridge, MR ;

Robertson, EG ;

Simons, JP .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (35) :6938-6949

[6] Spectroscopy of hydrogen-bonded formanilide clusters in a supersonic jet: Solvation of a model trans amide [J].

Fedorov, AV ;

Cable, JR .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (21) :4943-4952

[7]

Frisch J. M., 1998, GAUSSIAN 98 REVISION

[8] The shape of urea [J].

Godfrey, PD ;

Brown, RD ;

Hunter, AN .

JOURNAL OF MOLECULAR STRUCTURE, 1997, 413 :405-414

[9] Ion-dip spectroscopy and structure of 5-phenyl imidazole, 4-phenyl imidazole and its 1:1 hydrate [J].

Hockridge, MR ;

Robertson, EG ;

Simons, JP .

CHEMICAL PHYSICS LETTERS, 1999, 302 (5-6) :538-548

[10] Resistance to HIV protease inhibitors: A comparison of enzyme inhibition and antiviral potency [J].

Klabe, RM ;

Bacheler, LT ;

Ala, PJ ;

Erickson-Viitanen, S ;

Meek, JL .

BIOCHEMISTRY, 1998, 37 (24) :8735-8742

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