Bulletin of the Korean Chemical Society

  • 제10권5호
  • /
  • Pages.448-452
  • /
  • 1989
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Kinetic Studies on the Reactions of NADH Analogs : Effects of 3-Substituents of 1-benzyl-1,4-Dihydropyridines

  • 발행 : 1989.10.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

NADH analogs, 1-benzyl-3-substituted (X)-1,4-dihydropyridines 1-4 (1: X = $CONH_2$; 2: X = $CSNH_2$; 3: X = $COOCH_3$; 4: X = $COCH_3$) were synthesized. The second order rate constants for hydration reaction and oxidation reactions by $Cu^{2+}$, $Fe(CN)_6^{3-}$ or methylacridinium iodide (MAI) of the compounds were determined. For all reactions investigated, the rate constants increased with decreasing electronegative character of the 3-substituents of 1,4-dihydropyridines : the decreasing order of the reaction rates was 2>1>3>4. However, the sensitivity of the reaction rates on the 3-substituents differed among the reactions. This was explained in view of mechanisms of the reactions.

키워드

참고문헌

  1. Chem. Rev. v.82 D. M. Stout;A. I. Meyers
  2. Asymmetric Synthesis v.2 Y. Inouye;J. Oda;N. Baba;J. D. Morrison(ed.)
  3. Bioorg. Chem. v.14 S. Yasui;A. Ohno
  4. J. Am. Chem. Soc. v.80 A. G. Anderson;G. Berkelhammer
  5. J. Org. Chem. v.43 C. A. Bunton;F. Rivera;L. Sepulveda
  6. Bull. Korean Chem. Soc. v.8 K. K. Park;J. G. Yoo;J. W. Park
  7. J. Org. Chem. v.53 R. J. Kazlauskas
  8. J. Am. Chem. Soc. v.77 D. Mauzerall;F. H. Westheimer
  9. Biochemistry v.11 G. Mooser;H. Schulman;D. S. Sigman
  10. Bull. Korean Chem. Soc. v.9 J. W. Park;S. H. Yun;K. K. Park
  11. Kinetics and Mechanism J. W. Moore;R. G. Pearson
  12. J. Am. Chem. Soc. v.106 M. F. Powell;J. C. Wu;T. C. Bruice
  13. J. Chem. Soc. Chem. Comm. T. Okamoto;A. Ohno;S. Oka
  14. J. Am. Chem. Soc. v.95 D. J. Creighton;J. Hajdu;G. Mooser;D. S. Sigman
  15. J. Am. Chem. Soc. v.98 J. Hajdu;D. S. Sigman
  16. J. Am. Chem. Soc. v.103 A. Ohno;T. Shio;H. Yamamoto;S. Oka
  17. Bioorganic Chemistry v.12 J. W. Bunting;V. S. F. Chew;G. Chu;N. P. Fitzgerald;A. Gunasekara;H. T. P. Oh

피인용 문헌

  1. Complexation of NADH analogues with β-cyclodextrin: inhibitory effects of β-cyclodextrin against hydration and copper(II) and hexacyanoferrate(3–) oxidation of 1,4-dihyd vol.1991, pp.10, 1991, https://doi.org/10.1039/p29910001613
  2. Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry vol.4, pp.3, 2014, https://doi.org/10.1021/cs4011056