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Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques pp 227–270Cite as

Cyclopropane Compounds of Biological Interest

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Abstract

The cyclopropane ring is a relative newcomer to be recognized in natural products of biological interest, and to be applied synthetically to prospective biologically active compounds. The syntheses of biologically active cyclopropane derivatives have been studied only during the last 25 years. Ideas concerning the biosynthesis of naturally occurring cyclopropane compounds have been formulated still more recently. Although cyclopropane itself has been used as a general anesthetic in the clinic since 1930, more than 30 years passed before the first cyclopropane derivative, trans-2-phenylcyclopropylamine, became available in medicine. A number of cyclopropane fatty acids had turned up as constituents of certain lipids, but their origin and function did not become understood until much later. These slow developments contrast with the high level of activity in the purely chemical study of cyclopropane and its derivatives. Here the formation of such compounds from olefins or by photochemical reactions, and their ability to rearrange, have had high priority among organic chemists. Kinetic, theoretical, orbital-overlap, and bond-strain studies have also received considerably more attention than medicinal and biological investigations.

The preparation of this review has been aided by a grant, 12781, from the Institute of General Medical Sciences, National Institutes of Health, U.S.A.

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References

  1. A. Von Freund, Monatsh. Chem. 3, 625 (1882).

    Google Scholar 

  2. G. H. W. Lucas and V. E. Henderson, Canad. M. A. J. 21, 173 (1929).

    Google Scholar 

  3. V. E. Henderson and G. H. W. Lucas, Anesthesia and Analgesia 9, 1 (1930).

    Google Scholar 

  4. R. M. Waters and E. R. Schmidt, J. Am. Med. Assocn. 103, 975 (1934).

    Google Scholar 

  5. F. S. Orcutt and M. H. Seevers, J. Pharmacol. Exp. Therap. 59, 206 (1937).

    Google Scholar 

  6. T. S. Chambers and G. B. Kistiakowsky, J. Am. Chem. Soc. 56, 399 (1934).

    Google Scholar 

  7. B. H. Robbins, J. Pharmacol. Exp. Therap. 58, 243 (1936).

    Google Scholar 

  8. Beilsteins Handbuch der Organischen Chemie, Vol. V, 4th ed. ( Springer Verlag, Berlin 1963 ), p. 4.

    Google Scholar 

  9. L. Goodman and A. Gilman, The Pharmacological Basis of Therapeutics, 3rd ed. ( The McMillan Co., New York, N.Y., 1965 ), p. 75–81.

    Google Scholar 

  10. Pharmacology in Medicine, 3rd ed. (Ed. V. A. Drill, McGraw Hill, New York, N.Y., 1954 ), p. 119–122.

    Google Scholar 

  11. R. E. Tedeschi, D. H. Tedeschi, P. L. Ames, L. Cook, P. A. Mattis and E. J. Fellows, Proc. Soc. Exptl. Biol. Med. 102, 380 (1959).

    Google Scholar 

  12. D. H. Tedeschi, R. E. Tedeschi and E. J. Fellows, Proc. Soc. Exptl. Biol. Med. 103, 680 (1960).

    Google Scholar 

  13. A. Burger and W. L. Yost, J. Am. Chem. Soc. 70, 2198 (1948).

    Google Scholar 

  14. D. R. Maxwell, W. R. Gray and E. M. Taylor, Brit. J. Pharmacol. 17, 310 (1961).

    Google Scholar 

  15. H. Green and R. W. Erickson, J. Pharmacol. Exp. Therap. 129, 237 (1960).

    Google Scholar 

  16. A. R. Maas and M. J. Nimmo, Nature 754, 547 (1959).

    Google Scholar 

  17. M. Ozaki, H. Weissbach, A. Ozaki, B. Witkop and S. Udenfriend, J. Med. Pharm. Chem. 2, 591 (1960).

    Google Scholar 

  18. M. A. Schwartz, J. Pharmacol. Exp. Therap. 135, 1 (1962).

    Google Scholar 

  19. K. Stock and E. Westermann, Arch. Exptl. Pathol. Pharmakol. 243, 44 (1962).

    Google Scholar 

  20. E. A. Zeller and S. Sarkar, J. Biol. Chem. 237, 2333 (1962).

    Google Scholar 

  21. P. A. Shore and V. H. Cohn, Jr., Biochem. Pharmacol. 5, 91 (1960).

    Google Scholar 

  22. A. Burger and S. Nara, J. Med. Chem. 8, 859 (1965).

    Google Scholar 

  23. C. L. Zirkle, C. Kaiser, D. H. Tedeschi, R. E. Tedeschi and A. Burger, J. Med. Pharm. Med. 5, 1265 (1962).

    Google Scholar 

  24. C. Kaiser, B. M. Lester, C. L. Zirkle, A. Burger, C. S. Davis, T. J. Delia and L. Zirngibl, J. Med. Pharm. Chem. 5, 1243 (1962).

    Google Scholar 

  25. A. Burger, M. Bernabe and P. W. Collins, J. Med. Chem. 13, 33 (1970).

    Google Scholar 

  26. J. Finkelstein, E. Chang and J. Lee, J. Med. Chem. 8, 432 (1965).

    Google Scholar 

  27. J. Finkelstein, E. Chang, F. M. Vane and J. Lee, J. Med. Chem. 9, 319 (1966).

    Google Scholar 

  28. J. Finkelstein, E. Chang and J. Lee, J. Med. Chem. 9, 440 (1966).

    Google Scholar 

  29. A. Sjoerdsma, F. E. Smith, T. D. Stevenson and D. Udenfriend, Proc. Soc. Exptl. Biol. Med. 89, 36 (1955).

    Google Scholar 

  30. A. Burger, J. F. Siuda, N. Watzman and J.P. Buckley, J. Med.Chem. 12, 317 (1969).

    Google Scholar 

  31. L. O. Randall and R. E. Bagdon, Ann. New York Acad. Sci. 80, 626 (1959).

    Google Scholar 

  32. S. Sarkar, Dissertation, Northwestern University, Evanston, Illinois 1961.

    Google Scholar 

  33. For references see C. L. Zirkle and C. Kaiser, in: Psychopharmacological Agents (Ed. M. Gordon, Academic Press, New York, N.Y., 1964 ), p. 324.

    Google Scholar 

  34. H. Yamada and K. T. Yasunobu, J. Biol. Chem. 237, 1511 (1962).

    Google Scholar 

  35. C. M. Mcewen, Jr., J. Biol. Chem. 240, 2003, 2011 (1965).

    Google Scholar 

  36. P. Pratesi and H. Blaschko, Brit. J. Pharmacol. 14, 256 (1969).

    Google Scholar 

  37. E. Grana and L. Lilla, Brit. J. Pharmacol. 41, 501 (1959); (Ed. Farmaco, Pavia) Science 14, 605 (1959).

    Google Scholar 

  38. D. B. Hope and A. D. Smith, Biochem. J. 74, 101 (1960).

    Google Scholar 

  39. J. H. Biel, A. E. Drucker, T. F. Mitchell, P. S. Sprengeler, P. A. Nuhfer, A. C. Conway and A. Horita, J. Am. Chem. Soc. 81, 2805 (1959).

    Google Scholar 

  40. J. H. Biel, A. C. Conway, F. Dipierro, A. E. Drukker and P. A. Nuhfer, J. Am. Chem. Soc. 81, 4995 (1959).

    Google Scholar 

  41. A. Burger, C. S. Davis, H. Green, D. H. Tedeschi and C. Zirkle, J. Med. Pharm. Chem. 4, 571 (1961).

    Google Scholar 

  42. J. Augstein, S. M. Green, A. M. Monro, T. I. Wrigley, A. R. Katritzky and G. J. T. Tiddy, J. Med. Chem. 10, 391 (1967).

    Google Scholar 

  43. B. Belleau and J. Moran, J. Med. Pharm. Chem. 5, 215 (1962).

    Google Scholar 

  44. E. S. Lewis and C. E. Boozer, J. Am. Chem. Soc. 76, 791, 794 (1954).

    Google Scholar 

  45. E. A. Halevi and M. Nussim, J. Chem. Soc. 1963, 876.

    Google Scholar 

  46. M. J. S. Dewar, Hyperconjugation ( Ronald Press, New York, N.Y., 1962 ).

    Google Scholar 

  47. G. W. Cannon, A. A. Santilli and P. Shenian, J. Am. Chem. Soc. 81, 1660 (1959).

    Google Scholar 

  48. R. Fuchs and J. J. Bloomfield, J. Am. Chem. Soc. 81, 3158 (1959).

    Google Scholar 

  49. S. Sarkar, R. Banerjee, M. S. Ise and E. A. Zeller, Helv. Chim. Acta 43, 439 (1960).

    Google Scholar 

  50. C. Beard and A. Burger, J. Org. Chem. 26, 2335 (1961).

    Google Scholar 

  51. A. Burger and S. E. Zimmerman, Arzeimittel-Forsch. 16, 1571 (1966).

    Google Scholar 

  52. A. Burger and R. Bennett, J. Med. Pharm. Chem. 2, 687 (1960).

    Google Scholar 

  53. R. F. Long, Biochem. J. 82, 3 (1962).

    Google Scholar 

  54. J. J. Alleva, J. Med. Chem. 6, 621 (1963).

    Google Scholar 

  55. G. C. Heil, C. A. Leonard and D. H. Tedeschi, The Pharmacologist 7, 155 (1965).

    Google Scholar 

  56. C. Kaiser, C. A. Leonard, G. C. Heil, B. M. Lester, D. H. Tedeschi and C. L. Zirkle, J. Med. Chem. 13, 820 (1970).

    Google Scholar 

  57. A. M. Lands and T. G. Brown, Jr., in: Drugs Acting on the Peripheral Nervous System (Ed. A. Burger, Dekker, New York, N.Y., 1967 ), p. 422.

    Google Scholar 

  58. G. M. Simpson, J. Iqbal and F. Iqbal, Curr. Ther. Res. 8, 400 (1966).

    Google Scholar 

  59. J. H. Biel, in: Amphetamines and Related Compounds (Ed. E. Costa and S. Garattini, Raven Press, New York, N.Y., 1970 ), p. 14.

    Google Scholar 

  60. J. R. Boissier, R. Ratouis, C. Dumont and J. Lesbros, Chimica Therapeucita 5–6, 320 (1966).

    Google Scholar 

  61. R. E. Mcmahon, H. W. Culp and J. Mills, J. Med. Chem. 13, 986 (1970).

    Google Scholar 

  62. A. Burger, R. T. Standridge and E. J. Ariens, J. Med. Chem. 6, 211 (1963).

    Google Scholar 

  63. J. Mills, R. Kattau, I. H. Slater and R. W. Fuller, J. Med. Chem. 11, 95 (1968).

    Google Scholar 

  64. B. W. Horrum, U.S. Pat. 3, 037, 045 (1962).

    Google Scholar 

  65. T. A. Ban and H. E. Lehmann, Curr. Therap. Res. 8, 614 (1966).

    Google Scholar 

  66. L. G. Beregi, P. Hugon, J. C. Ledouarec, M. Laubie and J. Duhault, in: Amphetamines and Related Compounds (Ed. E. Costa and S. Garattini, Raven Press, New York, N.Y., 1970), p. 38, 40.

    Google Scholar 

  67. L. S. Harris, Arch. Exp. Pathol. Pharmakol. 248, 426 (1964).

    Google Scholar 

  68. L. S. Harris and A. K. Pierson, J. Pharmacol. Exptl. Therap. 143, 141 (1964).

    Google Scholar 

  69. Sterling Drug, Inc., Brit. Pat. 1,000,506 (1965); throughChem. Abstr. 63,16317/(1965).

    Google Scholar 

  70. For a review, see M. Gates, Sci. American 215, 131 (1966).

    Google Scholar 

  71. S.Archer, L. S.Harris, N. F. Albertson, B. F. Tullar and A.K.Pierson, in: Molecular Modification in Drug Design (Ed. F. W. Schueler, American Chemical Society, Washington, D.C., 1964 ), p. 166–168.

    Google Scholar 

  72. C. L. Zirkle and C. Kaiser, in: Medicinal Chemistry, 3rd ed. (Ed. A. Burger, Inter- science Division of John Wiley, New York, N.Y., 1970 ), p. 1430.

    Google Scholar 

  73. P. D. Armstrong and J. G. Cannon, J. Med. Chem. 13, 1037 (1970).

    Google Scholar 

  74. C. Y. Chou, J. P. Long, J. G. Cannon, and P. D. Armstrong, J. Pharmacol. Exptl. Therap. 166, 243 (1969).

    Google Scholar 

  75. C. Chothia and P. Pauling, Nature 226, 541 (1970).

    Google Scholar 

  76. P. Waser, Experientia 17, 300 (1971).

    Google Scholar 

  77. A. H. Beckett, Ann. N.Y. Acad. Sci. 44, 675 (1967).

    Google Scholar 

  78. A. Burger and B. R. Bedford, J. Med. Chem. 6, 402 (1963).

    Google Scholar 

  79. J. F. Mccarthy, J. G. Cannon, J. P. Buckley and W. J. Kinnard, J. Med. Chem. 7, 72 (1964).

    Google Scholar 

  80. A. Burger and H.-J. Petersen, J. Med. Chem. 7, 562 (1964).

    Google Scholar 

  81. R. A. Pages and A. Burger, J. Med. Chem. 9, 766 (1966).

    Google Scholar 

  82. R. A. Pages and A. Burger, J. Med. Chem. 10, 435 (1967).

    Google Scholar 

  83. D. G. Markees and A. Burger, J. Am. Chem. Soc. 70, 3329 (1948).

    Google Scholar 

  84. D. G. Markees and A. Burger, J. Am. Chem. Soc. 71, 2031 (1949).

    Google Scholar 

  85. J. R. Boissier, R. Ratouis, C. Dummont, P. H. Derible and J.-P. Lavaux, J. Med. Chem. 13, 971 (1970).

    Google Scholar 

  86. A. F. Crowther, D. J. Gilman, B. J. Mcloughlin, L. M. Smith, R. W. Turner and T. M. Wood, J. Med. Chem. 12, 638 (1969).

    Google Scholar 

  87. C. H. Tilford, M. G. Van Campen, Jr., and R. S. Shelton J. Am. Chem. Soc. 69, 2902 (1947).

    Google Scholar 

  88. J. W. Dean, G. O. Potts and R. G. Christiansen, J. Med. Chem. 10, 795 (1967).

    Google Scholar 

  89. G. W. Moersch, D. E. Evans and G. S. Lewis, J. Med. Chem. 10, 254 (1967).

    Google Scholar 

  90. J. Fried, C. Beard, I.T. Harrison, I. Jamieson, W.Rooks and R. Dorfman, as reported in: Chem. Eng. News, 25 Sept. 1967, p. 56.

    Google Scholar 

  91. M. E. Wolff, W. Ho and R. Kwok, J. Med. Chem. 7, 577 (1964).

    Google Scholar 

  92. G. Ourisson, P. Crabbe and O. Rodig, Tetracyclic Triterpenes ( Holden-Day, San Francisco, Calif., 1961, 1964 ).

    Google Scholar 

  93. W. Parker, J. S. Roberts and R. Ramage, Quarterly Rev. 21, 331 (1967).

    Google Scholar 

  94. For a review, see F. L. Carter and V. L. Frampton, Chem. Revs. 64, 497 (1964) (p. 521 ).

    Google Scholar 

  95. K. Hofmann and T. Y. Liu, Biochim. Biophys. Acta 37, 364 (1960).

    Google Scholar 

  96. K. J. I. Chalk and E. Kodicek, Biochim. Biophys. Acta 50, 579 (1961).

    Google Scholar 

  97. W. M. O’Leary, J. Bact. 77, 367 (1959).

    Google Scholar 

  98. M. Gastambide-Odier, J. M. Delaumeny and E. Lederer, Compt. rend. Acad. Sci. (Paris) 259, 3404 (1964).

    Google Scholar 

  99. A. H. Etemadi, A. M. Miquel, E. Lederer and M. Barbier, Bull. soc. chim. France 1964, 3274.

    Google Scholar 

  100. A. E. Chung and J. H. Law, Biochemistry 3, 967, 1989 (1964).

    Google Scholar 

  101. J. H. Law and J. G. Hildebrand, Biochemistry 3, 1304 (1964).

    Google Scholar 

  102. W. M. O’Leary, on: Transmethylation and Methionine BiosynthesisW. M. O’Leary (Ed. S. K. Shapiro and F. Schlenk, The University of Chicago Press, Chicago, 111., 1965 ), p. 94.

    Google Scholar 

  103. S. Pohl, J. H. Law, and R. Ryhage, Biochim. Biophys. Acta 70, 583 (1963).

    Google Scholar 

  104. E. Lederer, Biochem. J. 93, 449 (1964).

    Google Scholar 

  105. E. Lederer, in: Impact of Basic Sciences on Medicine (Ed. B. Shapiro and M. Pywes, Academic Press, New York, N.Y., 1966 ), p. 51–69.

    Google Scholar 

  106. G. Halphen, J. Pharm. [6] 6, 390 (1897); J. Chem. Soc. 74, 358 (1898).

    Google Scholar 

  107. See ref. [93], p. 513–514.

    Google Scholar 

  108. G. Dijkstra and H. J. Duin, Nature 176, 71 (1955).

    Google Scholar 

  109. F. D. Gunstone, Chem. Ind. ( London ) 1955, 1476.

    Google Scholar 

  110. J. R. Nunn, J. Chem. Soc. 1952, 313.

    Google Scholar 

  111. H. E. Simmons and R. D. Smith, J. Am. Chem. Soc. 81, 4256 (1959).

    Google Scholar 

  112. N. T. Castellucci and C. E. Griffin, J. Am. Chem. Soc. 82, 4107 (1960).

    Google Scholar 

  113. P. J. Schaible and S. L. Bandemer, Poultry Sci. 25, 451 (1946).

    Google Scholar 

  114. F. W. Lorenz and H. J. Almquist, Ind. Eng. Chem. 26, 1311 (1934).

    Google Scholar 

  115. J. C. Masson, M. G. Vavich, B. W. Heywang and A. R. Kemmerer, Science 126, 751 (1957).

    Google Scholar 

  116. F. S. Shenstone and J. R. Vickery, Nature 177, 94 (1956).

    Google Scholar 

  117. F. S. Shenstone and J. R. Vickery, Poultry Sci. 38, 1055 (1959).

    Google Scholar 

  118. D. L. Schneider, M. G. Vavich, A. A. Kurnick and A. R. Kemmerer, Poultry Sci. 40, 1644 (1961).

    Google Scholar 

  119. D. L. Schneider, A. A. Kurnick, M. G. Vavich and A. R. Kemmerer, J. Nutr. 77, 403 (1962).

    Google Scholar 

  120. R. J. Evans, J. A. Davidson, J. N. La Rue and S. L. Bandemer, Poultry Sci. 62, 875 (1963).

    Google Scholar 

  121. H. W. Kircher, J. Am. Oil. Chemists’ Soc. 41, 4 (1964).

    Google Scholar 

  122. H. Veldstra, Enzymologia 11, 97, 137 (1944).

    Google Scholar 

  123. H. Veldstra and H. L. Booy, Biochim. Biophys. Acta 3, 278 (1949).

    Google Scholar 

  124. H. Veldstra and C. van de Westeringh, Ree. trav. chim. Pays-Bas 70, 1113, 1127 (1951).

    Google Scholar 

  125. H. L. Booy and H. Veldstra, Biochim. Biophys. Acta 3, 260 (1949).

    Google Scholar 

  126. H. Veldstra, Bull. soc. chim. biol. 31, No. 3–4 (1949).

    Google Scholar 

  127. W. A. Gersdorff, J. Econ. Entom. 42, 532 (1949).

    Google Scholar 

  128. L. Crombie, J. Imp. Coll. Chem. Soc. 32, 40 (1953).

    Google Scholar 

  129. K. Yamaguchi, J. Japan. Chem. 4, 583 (1950); 5, 141, 262 (1951).

    Google Scholar 

  130. W. Sobötka, Przemysl Chem. 35, 496 (1956).

    Google Scholar 

  131. M. Schechter, N. Green and F. La Forge, J. Amer. Chem. Soc. 71, 3165 (1949).

    Google Scholar 

  132. H. Jaffe and J. L. Neumeyer, J. Med. Chem. 13, 901 (1970).

    Google Scholar 

  133. M. C. Crew, M. D. Melgar and L. J. Haynes, J. Pharm. Sci. 58, 960 (1969).

    Google Scholar 

  134. L. J. Hekimian, S. Gershon and A. Floyd, Arzneimittel-Forsch. 19, 955 (1969).

    Google Scholar 

  135. J. E. Villarreal and M. H. Seevers, Addendum to the Minutes of the 31st Meeting of the Committee of Problems of Drug Dependence, Natl. Acad. Sci., U.S.A. (1969).

    Google Scholar 

  136. W. F. Michne and N. F. Albertson, J. Med. Chem. 12, 402 (1969).

    Google Scholar 

  137. R. Wiechert, H. Laurent and H. Hofmeister, Rev. Soc.Chim.Mex. XIII, 73 A (1969).

    Google Scholar 

  138. R. Wiechert and F. Neumann, Arzneimittel-Forsch. 15, 244 (1965).

    Google Scholar 

  139. H. Laurent, G. Schulz and R. Wiechert, Chem. Ber. 102, 2570 (1969).

    Google Scholar 

  140. H. Saunders and F. J. Ebling, J. Invest. Dermatol. 52, 163 (1969); F. J. Ebling, Proc. Roy. Soc. Med. 62, 890 (1969).

    Google Scholar 

  141. R. L. Hale, J. Leclercq, B. Tursch, C. Djerassi, R. A. Gross, Jr., A. J. Weinheimer, P. Gupta and P. J. Scheuer, J. Amer. Chem. Soc. 92, 2179 (1970).

    Google Scholar 

  142. F. J. Schmitz and T. Pattabhiraman, quoted in: C. and E. News, 12 October 1970, p. 35.

    Google Scholar 

  143. R. H. Mizzoni, F. Goble, E. Konopka, J. Gelzer, J. Szanto, D. C. Maplesden, J. E. Brown, J. Boxer, G. Zaunius, J. B. Ziegler and G. De Stevens, J. Med. Chem. 13, 870 (1970).

    Google Scholar 

  144. R. H. Mizzoni, R. A. Lucas, R. Smith, J. Boxer, J. E. Brown, F. Goble, E. Konopka, J. Gelzer, J. Szanto, D. C. Maplesden and G. De Stevens, J. Med. Chem. 13, 878 (1970).

    Google Scholar 

  145. E. F. Rogers, Ann. N.Y. Acad. Sci. 98, 412 (1962).

    Google Scholar 

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  1. Department of Chemistry, University of Virginia, Charlottesville, Virginia, 22901, USA

    Alfred Burger

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    Ernst Jucker

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Burger, A. (1971). Cyclopropane Compounds of Biological Interest. In: Jucker, E. (eds) Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques. Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques, vol 15. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7078-8_7

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