Skip to main content

Synthese und zytostatische Wirkung von N-Lost-Derivaten

Part of the Fortschritte der Chemischen Forschung book series (TOPCURRCHEM,volume 7/1)

This is a preview of subscription content, access via your institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • DOI: 10.1007/BFb0051785
  • Chapter length: 37 pages
  • Instant PDF download
  • Readable on all devices
  • Own it forever
  • Exclusive offer for individuals only
  • Tax calculation will be finalised during checkout
eBook
USD   54.99
Price excludes VAT (USA)
  • ISBN: 978-3-540-37156-4
  • Instant PDF download
  • Readable on all devices
  • Own it forever
  • Exclusive offer for individuals only
  • Tax calculation will be finalised during checkout
Softcover Book
USD   69.99
Price excludes VAT (USA)

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. Aiko, I., S. Owari, and M. Torigoe: Nitrogen Mustard N-oxide and its effect on the Yoshida sarcoma. J. Pharm. Soc. Japan 72, 1297 (1952).

    CAS  Google Scholar 

  2. Arnold, H., u. H. Bekel: Die Oxazolidon-Reaktion von 2-Chloräthylsubstituierten sekundären Aminen. Arzneimittel-Forsch. 14, 750 (1964).

    CAS  Google Scholar 

  3. -u. F. Bourseaux: Synthese und Abbau cytostatisch wirksamer cyclischer N-Phosphamidester des Bis-(Β-chloräthyl)-amins. Angew. Chem. 70, 539 (1958).

    CrossRef  CAS  Google Scholar 

  4. --: Synthese des N,N-Bis-(2-chloräthyl)-O-(3-amino-propyl)-phosphorsäureamidoesters. Arzneimittel-Forsch. 13, 927 (1963).

    CAS  Google Scholar 

  5. --u. N. Brock: über Beziehungen zwischen chemischer Konstitution und cancerotoxischer Wirkung in der Reihe der Phosphamidester des Bis-(Β-chloräthyl)-amins. Arzneimittel-Forsch. 11, 143 (1951).

    Google Scholar 

  6. -u. H. Klose: über den hydrolytischen Abbau des hexacyclischen N-Lostphosphamidesters B 518 unter physiologischen Bedingungen. Arzneimittel-Forsch. 11, 159 (1961).

    CAS  Google Scholar 

  7. -u. J. Venjakob: Formaldehyd-Abbau von Bis-(Β-chloräthyl)-methylamin-N-oxyd. Arzneimittel-Forsch. 5, 722 (1955).

    CAS  Google Scholar 

  8. -, N. Brock u. H.-J. Hohorst: Untersuchungen zum Abbau von N-Oxyd-Lost in wäßriger Lösung. Arzneimittel-Forsch. 7, 735 (1957).

    CAS  Google Scholar 

  9. Bergel, F., and J. A. Stock: Cyto-active Amino-Acid and Peptide Derivatives. Part I. Substituted Phenylalanines. J. chem. Soc. 1954, 2409.

    Google Scholar 

  10. --Cyto-active Amino-acids and Peptides. Part IV. Synthesis of α[p-Di-(2-chloroethyl)-amino-benzylidene-and-benzyl-]-hippuramides and-hippuramido-acids. J. chem. Soc. 1957, 4563.

    Google Scholar 

  11. --Cyto-active Amino-acids and Peptides. Part VIII. Nα-Acyl, Amide, Ester and Peptide Derivatives of Melphalan. J. chem. Soc. 1960, 3658.

    Google Scholar 

  12. -and R. Wade Cyclo-active Amino-acids and Peptides. Part VII. Derivatives of Serine and Threonine. J. chem. Soc. 1959, 941.

    Google Scholar 

  13. Billman, J. H., and J. L. Meisenheimer: Hexahydropyrimidines IV. Syntheses of 2-[4-(N,N-Bis-(2-chloroethyl)-amino)-aryl]-1,3-bis-(aralkyl)-hexahydropyrimidines as Antitumor Agents. J. Med. Chemistry 7. 115 (1964).

    CrossRef  CAS  Google Scholar 

  14. Bratzel, R. P., R. B. Ross, Th. H. Goodridge, W. T. Huntress, M. T. Flather, and D. E. Johnson: Survey of Nitrogen Mustards. Cancer Chemotherapy Reports 1963, 1–511.

    Google Scholar 

  15. Brock, N.: Zur pharmakologischen Charakterisierung zyklischer N-LostPhosphamidester als Krebs-Chemotherapeutica. Arzneimittel-Forsch. 8, 1 (1958).

    CAS  Google Scholar 

  16. -, und H.-J. Hohorst: Reaktionen von Bis-(Β-chloräthyl)-amin in vitro und in vivo. Arzneimittel-Forsch. 11, 164 (1961).

    CAS  Google Scholar 

  17. --: über die Aktivierung von Cyclophosphamid im Warmblüterorganismus. Naturwiss. 49, 610 (1962).

    CrossRef  CAS  Google Scholar 

  18. --: über die Aktivierung von Cyclophosphamid in vivo und in vitro. Arzneimittel-Forsch. 13, 1021 (1963).

    CAS  Google Scholar 

  19. Brookes, P., and P.D.Lawley: The Alkylation of Guanosine and Guanylic Acid. J. chem. Soc. 1961, 3923.

    Google Scholar 

  20. Dall'Asta, L., u. P. Ferrario: Synthetische Versuche in der Gruppe der cytostatisch wirksamen Substanzen. Darstellung von Dl-und l-3-[Di(Β-chloräthyl)-amino]-4-hydroxy-phenylalanin. Helv. chim. Acta 45, 1065 (1962).

    CrossRef  Google Scholar 

  21. Davis, W., J. J. Roberts, and W. C. J. Ross: Aryl-2-halogeno-alkylamines. Part XIII. Chloroethylamino-derivatives of Some Phenoxyalkanoic Acids and of Some Substituted α-Amino-acids. J. chem. Soc. 1955, 890.

    Google Scholar 

  22. DeGraw, J., and L. Goodman: Potential Anticancer Agents. LXXII. Alkylating Agents Derived from Indole. II. Synthesis of a Nitrogen Mustard Derived from Dl-Tryptophan. J. org. Chemistry 27, 1395 (1962).

    CrossRef  CAS  Google Scholar 

  23. --: Alkylating Agents Derived from Indole. IV. Synthesis of the 5-Nitrogen Mustard of Indole-3-carboxylic Acid. J. med. Chemistry 7, 213 (1964).

    CrossRef  CAS  Google Scholar 

  24. Eisleb, O.: Neue Synthesen mittels Natriumamids. Ber. dtsch. chem. Ges. 74, 1433 (1941).

    CrossRef  Google Scholar 

  25. Everett, J. L., J. J. Roberts, and W. C. J. Ross: Aryl-2-halogenoalkylamines Part XII. Some Carboxylic Derivatives of NN-Di-2-chloroethylaniline. J. chem. Soc. 1953, 2386.

    Google Scholar 

  26. Foley, G. E., O. M. Friedman, and B. P. Drolet: Studies on the Mechanism of Action of Cytoxan Evidence of Activation in Vivo and in Vitro. Cancer Research 21, 57 (1961).

    CAS  Google Scholar 

  27. Friedman, O. M., and E. Boger: Colorimetric Estimation of Nitrogen Mustards in Aqueous Media. Hydrolytic Behavior of bis(beta-chloroethyl)-Amine, nor NH2. Analyt. Chem. 33, 906 (1961).

    CrossRef  CAS  Google Scholar 

  28. -, K. Pollak, and E. Khedouri: 1-(Β-Chloroethyl)-3-carbamylpyridinium Chloride. Prototype of a New Class of Latently Cytotoxic Potential Antitumor Agents. J. med. Chemistry 6, 462 (1963).

    CrossRef  CAS  Google Scholar 

  29. -, and A. M. Seligman: Preparation of Secondary Amine Mustards with High Toxicity. J. Amer. chem. Soc. 76, 658 (1954).

    CrossRef  CAS  Google Scholar 

  30. Gilman, A., and F. S. Philips: The biological actions and therapeutic applications of Β-chloroethyl-amines and sulfides. Science 103, 409 (1946).

    CrossRef  CAS  Google Scholar 

  31. Golumbic, C., J. S. Fruton, and M. Bergmann: Chemical Reactions of the Nitrogen Mustard Gases. I. The Transformations of Methyl-Bis(Βchloroethyl)-amine in Water. J. org. Chemistry 11, 518 (1946).

    CrossRef  CAS  Google Scholar 

  32. Goodman, L., R. R. Spencer, G. Casini, O. P. Crews, and E. J. Reist: Synthesis of 6-and 7-Bis-(2-chloroethyl)-amino-Dl-tryptophan. J. med. Chemistry 8, 251 (1965).

    CrossRef  CAS  Google Scholar 

  33. Hohorst, H.-J., A. Ziemann u. N. Brock: Alkylierende Substanzen in Serum und Urin nach Injektion von Cyclophosphamid. Arzneimittel-Forsch. 15, 432 (1965).

    CAS  Google Scholar 

  34. Ishidate, M., K. Kobayashi, Y. Sakuray, H. Sato, and T. Yoshida: Chemotherapy of malignant growth employing Yoshida sarcoma animals. II. Effect of N-oxide derivatives of nitrogen mustard. Proc. Jap. Acad. 27, 493 (1951).

    CAS  Google Scholar 

  35. -, Y. Sakurai, and Y. Kuwada: Cancerocidal substances. XXIX. 1,1-, Bis-(2-chloroethyl)-hydrazine and its derivatives as tumor-inhibiting agents. Chem. Pharm. Bull. (Tokyo) 8, 543 (1960).

    CAS  Google Scholar 

  36. Iwamoto, R. H., E. M. Acton, L. Goodman, and B. R. Baker: Potential Anticancer Agents. LXIV. Alkylating Agents Related to Phenylalanine Mustard. V. A Cyclic Phosphorodiamidate Related to Cytoxan. J. org. Chemistry 26, 4743 (1961).

    CrossRef  CAS  Google Scholar 

  37. Johnson, J. M., and J. A. Stock: Cyto-active Amino-acids and Peptides. Part X. A Pentapeptide and a Basic Dipeptide from Melphalan. J. chem. Soc. 1962, 3806.

    Google Scholar 

  38. Johnston, Th. P., L. B. Holum, and J. A. Montgomery: Synthesis of Potential Anticancer Agents. XVI. S-Substituted Derivatices of 6-Mercaptopurine. J. Amer. chem. Soc. 80, 6265 (1958).

    CrossRef  CAS  Google Scholar 

  39. Khedouri, E., Young-Ho Kim, and O. M. Friedman: N,N-Bis-(2-chloroethyl)-carbamoyl Derivatives of l-Amino-Acids. New Potential Antitumor Agents with Latent Activity. J. med. Chemistry 7, 653 (1964).

    CrossRef  CAS  Google Scholar 

  40. Koppel, H. C., R. H. Springer, R. K. Robins, F. H. Schneider, and C. C. Cheng: Synthesis of Some 8-Substituted Bis(Β-chloroethyl)-amino Derivatives of Naturally Occurring N-Methylated Purines. J. org. Chemistry 27, 2173 (1962).

    CrossRef  CAS  Google Scholar 

  41. Larionov, L. F.: Acta Un. Int. Cancer 13, 393 (1957).

    CAS  Google Scholar 

  42. -: Peptides, Amides, and Esters of Chloroethylamino Derivatives of Amino Acids and of Phenylalkancarboxylic Acids. A new Class of Antitumor Compounds. Cancer Research 21, 99 (1961).

    CAS  Google Scholar 

  43. -, E. N. Shkodinskaja, V. I. Troosheikina, A. S. Khokhlov, O. S. Vasina, and M. A. Novikova: Studies on the Anti-Tumour Activity of p-Di-(2-chloroethyl)-Aminophenylalanine (Sarcolysine). Lancet 1955 II, 169.

    CrossRef  Google Scholar 

  44. Levin, G., K. Sugiura, and G. B. Brown: A Nitrogen Mustard Derivative of 6-Mercaptopurine. J. med. Chemistry 7, 357 (1964).

    CrossRef  CAS  Google Scholar 

  45. Lyttle, D. A., and H. G. Petering: 5-Bis-(2-chloroethyl)-Aminouracil. A new Antitumor Agent. J. Amer. chem. Soc. 80, 6459 (1959).

    CrossRef  Google Scholar 

  46. Martinez, A. P., W. W. Lee, and L. Goodman: Phosphorylated Alkylating Agents Related to Dl-Phenylalanine. J. med. Chemistry 7, 224 (1964).

    CrossRef  CAS  Google Scholar 

  47. Preussmann, R.: Chlor-Abspaltbarkeit und Wirksamkeit von N-Lost-Verbindungen. Arzneimittel-Forsch. 8, 9 (1958).

    CAS  Google Scholar 

  48. -: Chlor-Abspaltbarkeit und Wirksamkeit bei N-Lost Verbindungen. Arzneimittel-Forsch. 12, 260 (1962).

    CAS  Google Scholar 

  49. -, C. Satzinger u. D. Schmähl: N,N-Bis-(Β-chloräthyl)-hydrazin und seine cancerotoxische Wirksamkeit. Angew. Chem. 70, 743 (1958).

    CrossRef  CAS  Google Scholar 

  50. Rauen, H. M.: Die Bildungsgeschwindigkeiten von N-Β-Halogenäthylaziridinen aus Bis-(Β-halogen-äthyl)-aminen unter physiologischen Bedingungen. Arzneimittel-Forsch. 14, 855 (1964).

    CAS  Google Scholar 

  51. Reist, E. J., R. R. Spencer, L. Goodman, and B. R. Baker: Potential Anticancer Agents. LXVIII. Synthesis of Alkylating Agents Derived from 3-Amino-3-deoxy-D-allose. J. org. Chemistry 27, 202 (1962).

    CrossRef  CAS  Google Scholar 

  52. Ross, L. O., W. W. Lee, M. G. M. Schelstraete, L. Goodman, and B. R. Baker: Potential Anticancer Agents, LVI. Synthesis of 5-[Bis-(2-chloroethyl)-aminomethyl]-uracil. J. org. Chemistry 26, 3021 (1961).

    CrossRef  CAS  Google Scholar 

  53. Ross, W. C. J., G. P. Warwick, and J. J. Roberts: Aryl-2-halogenalkylamines. Part XIV. Some Compounds possessing Latent Cytotoxic Activity. J. chem. Soc. 1955, 3110.

    Google Scholar 

  54. -and J. G. Wilson: Some NN-Di-2-chloroalkyl Derivatives of Carboxyamides and Sulphonamides. J. chem. Soc. 1959, 3616.

    Google Scholar 

  55. Schweer, K. H.: Die Darstellung von im Esteramidring mit 14C und 32P markiertem [Bis-(Β-chlor-äthyl)-amido]-phosphorsäure-N,O-trimethylen-esteramid (Endoxan®). Chem. Ber. 95, 1799 (1962).

    CrossRef  CAS  Google Scholar 

  56. Skinner, Ch. G., T. J. McCord, J. M. Ravel, and W. Shive: O-Carbamyl-l-serine, an Inhibitory Analog of l-Glutamine. J. Amer. chem. Soc. 78, 2412 (1956).

    CrossRef  CAS  Google Scholar 

  57. Stahmann, M. A., and M. Bergmann: Chemical Reactions of the Nitrogen Mustard Gases. VIII. The Oxidation of the Nitrogen Mustard Gases by Peracids. J. org. Chemistry 11, 586 (1946).

    CrossRef  CAS  Google Scholar 

  58. Steiner, B., H. Arnold, E. H. Graul, H. Bekel, H. Hundeshagen u. H. Wilmanns: Zur Synthese von tritiummarkiertem Cyclophosphamid (einem Krebschemotherapeuticum) hoher spezifischer Aktivität. Atompraxis 10, 358 (1964).

    CAS  Google Scholar 

  59. Vargha, L.: über neue Zuckerderivate mit zytostatischer Wirksamkeit. Naturwiss. 42, 582 (1955).

    CrossRef  CAS  Google Scholar 

  60. -ö. Feher, and S. Lendval: Synthesis of New Sugar Derivatives of Potential Antitumour Activity. Part II. Di-2-(chloroethyl)-D-glucosamine Hydrochloride. J. chem. Soc. 1957, 810.

    Google Scholar 

  61. -L. Toldy, ö. Feher, and S. Lendval: Synthesis of New Sugar Derivatives of Potential Antitumour Activity. Part I. Ethylene-imino-and 2-Chloroethylamino-derivatives. J. chem. Soc. 1957, 805.

    Google Scholar 

  62. Vita, G., L. Monti, and R. Angelucci: Synthesis of N6,N6-Bis(2-chloroethyl)-Dl-lysine. J. med. Chemistry 7, 468 (1964)

    CrossRef  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and Permissions

Copyright information

© 1966 Springer-Verlag

About this paper

Cite this paper

Arnold, H. (1966). Synthese und zytostatische Wirkung von N-Lost-Derivaten. In: Organische Chemie. Fortschritte der Chemischen Forschung, vol 7/1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0051785

Download citation

  • DOI: https://doi.org/10.1007/BFb0051785

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-03511-4

  • Online ISBN: 978-3-540-37156-4

  • eBook Packages: Springer Book Archive