PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Geometry of alfa-Diaryl Type CH-NH Acids of Pharmacological Interest. Crystal Structures of alfa-(4-Chlorophenyl)- and alfa-(2,4-Dichlorophenyl-alfa-2-pyrazilideneacetonitrilles

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
alfa-Diarylacetonitriles represent a very interesting model for studying the structure-activity relationship, due to restricted freedom of conformational diversity and, on the other hand, a very wide range of biological activities, including analgesic, non-narcotic antiinflammatory and antirheumatic. The two studied representatives have in the crystal state very uniform molecular structures, which may be characterized by a dihedral angle between the two aromatic rings, being 77 graduate in 4-chlorophenyl; 74 graduate and 80 graduate in 2,4-dichlorophenyl derivative, respectively. Despite the presence of groups capable of weak C-H hydrogen bonds formation there is only one short C-H...X contact (X = N in 4 position of the pyrazinyl ring) of 2.40 ?, being significantly shorter than the sum of van der Waals radii of respective atoms. The contact found in the 2,4-dichlorophenyl derivative crystal is in accord with CH-NH proton transfer observed in these compounds.
Słowa kluczowe
Rocznik
Strony
1275--1284
Opis fizyczny
Bibliogr. 35 poz., rys.
Twórcy
autor
  • Institute of General and Ecological Chemistry, Technical University of Łódź,ul. Żeromskiego 116, 90-924 Łódź, Poland
autor
  • Institute of General and Ecological Chemistry, Technical University of Łódź,ul. Żeromskiego 116, 90-924 Łódź, Poland
autor
  • Institute of General and Ecological Chemistry, Technical University of Łódź,ul. Żeromskiego 116, 90-924 Łódź, Poland
autor
  • Institute of General and Ecological Chemistry, Technical University of Łódź,ul. Żeromskiego 116, 90-924 Łódź, Poland
  • Institute of General and Ecological Chemistry, Technical University of Łódź,ul. Żeromskiego 116, 90-924 Łódź, Poland
autor
  • Department of Organic Chemistry, Medical University of Gdañsk, Al. Hallera 107, 80-416 Gdańsk, Poland
Bibliografia
  • 1.Junek H., Monatsh. Chem., 96, 2046 (1965).
  • 2.Junek H., Monatsh. Chem., 95, 1201 (1964).
  • 3.Junek H., Monatsh. Chem., 95, 1473 (1964).
  • 4.Gutsche C.D. and Voges H.W., J. Org. Chem., 32, 2685 (1967).
  • 5.Ishiguro Y., Funakoshi K., Sachi S. and Hamana M., Heterocycles, 14, 179 (1980).
  • 6.Borror A.L. and Hacberer A.F.,.J. Org. Chem., 30, 243(1965).
  • 7.Lapatshev W.W., Zaguliaieva O.A. and Mamaiev W.P., Khim. Geterotsikl. Soedin., 11, 1544 (1978).
  • 8.Siedova W.F. and Mamaiev W.P., Khim. Geterotsikl. Soedin., 6, 827 (1979).
  • 9.Mandelli R. and Merlini L., Tetrahedron, 22, 3253 (1966).
  • 10.Pomove N.D.,.J. Med. Chem., 11,431 (1968).
  • 11.Wisterowicz K., Foks H., Strzałkowska-Grad H., Hać E., Janowiec M. and Zwolska-Kwiek Z., Acta Polon. Pharm., 43, 25 (1986).
  • 12.Treu M., Jordis U. and Lee V.J., Molecules, 6, 959 (2001).
  • 13.YamadaT., Nobuhara Y., Shimamura H., Yoshihara K., Yamaguchi A. and Ohki M., Chem. Pharm. Bull., 29, 3433 (1981).
  • 14.Cardellini M., Claudi F., Pcrlini V., Balduini W., Cattabcni F. and Cimino M., Farmaco Ed. Sei., 42,307 (1987).
  • 15.Deuch H.M., Shi Q., Gruszecka-Kowalik E. and Schweri M.M., J. Med. Chem., 39. 1201 (1996). 16.Kalritzky A.R., Yannakopoulou K., Thomson I., Sączewski F. and Pilarski B., J. Chem. Engineering Data, 32, 479 (1987).
  • 17.Pilarski B. and Foks H., Polish Patent, No. 137 869 (1986).
  • 18.Pilarski B. and Foks H., Polish Patent. No. 135 250 (1986).
  • 19.Pilarski B., Foks H., Osmialowski K. and Kaliszan R., Monatsh. Chem., 115, 179 (1984).
  • 20.Petrusewicz J., Siluk D., Kaliszan R., Foks H. and Nowakowska E., Acta Polon. Pharm.- Drug Res., 56.463(1999).
  • 21.Petrusewicz J., Turowski M„ Foks H.. Pilarski B. and Kaliszan R., Life Sci., 56, 667 (1995).
  • 22.Petrusewicz J., Yilinkou R.G., Pilarski B. and Kaliszan R., Pharmacology Toxicology, 70,448 (1992).
  • 23.Allen F.H., Acta Cryst., B58, 380 (2002), Cambridge Structural Database, Ver. 5.25.
  • 24.Duthie A., Scammells P., Katsifis A. and Tiekink E.R.T., Acta Cryst., E57, ol04 (2001).
  • 25.Wang A., Tandcl S., Zhang H., Huang Y„ Holdeman T.C. and Biehl E.R., Tetrahedron, 54,3391 (1998).
  • 26.KM4 Manual, Version 3.1 (2002).
  • 27.Sheldrick G.M., SIIELXS, Program for Crystal Structure Solution. University of Gottingen, German (1997).
  • 28.Sheldrick G.M., SHELXL, Program for Refinement of Crystal Structures. University of Gottingen, Germany (1997).
  • 29.DISCOVER 2.9.7 User Guide, San Diego: Biosym/MSI (1995).
  • 30.de Meester P., Khanapure S.P., Chu S.S.C. and Biehl E.R.. Acta Cryst., C43, 370 (1987).
  • 31.Siriwardane U., Khanapure S.P., Chu S.S.C. and Biehl E.K.,Acta Cryst., C43, 2246 (1987).
  • 32.Jarikov V.V. and Neckers D.C., J. Org. Chem., 66, 659(2001).
  • 33.Zhang H., Refat H.M. and Biehl E.R., Acta Cryst., C51, 1667 (1995).
  • 34.Iravani E. and Ncumullcr B., Organometallics, 22,4129 (2003).
  • 35.SHELXTL PC, Siemens Analytical X-Ray Instruments Inc. (1990).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0139
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.