Journals / Turkish Journal of Chemistry / 2007 / Cilt: 31 - Sayı: 2

Synthesis of 2-Acylamino, 2-Aroylamino and Ethoxycarbonyl Imino-1,3,4-thiadiazoles as Antitumor Agents

Pages
125–134
Publication Date
2007-02-01
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The in vitro antitumor activities of some selected compounds were screened and compounds 2a, 2b, 2c, 3a, 3b, 3c, 5a, 5b and 5c were found to be active.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:2-Amino-1,3,4-thiadiazoles compounds (2a-e) were obtained from the reaction of thiosemi carbazide with 2-cyanomethoxyphenoxyacetonitriles (1).
📊
Key Findings & Data:Mono acylamino, mono aroylamino and diethoxycarbonyl imino-1,3,4-thiadiazole compounds (3a-e, 4a-e, 5a-c) were synthesized via the reaction of 2-amino-1,3,4-thiadiazole compounds (2a-e) with acetyl chloride or acetic anhydride, benzoyl chloride or benzoic anhydride and ethyl chloroformate, respectively.
💡
Conclusion & Impact:The in vitro antitumor activities of some selected compounds were screened and compounds 2a, 2b, 2c, 3a, 3b, 3c, 5a, 5b and 5c were found to be active.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:4-Thiadiazole · acetyl chloride · benzoyl chloride

Abstract

2-Amino-1,3,4-thiadiazoles compounds (2a-e) were obtained from the reaction of thiosemi carbazide with 2-cyanomethoxyphenoxyacetonitriles (1). Mono acylamino, mono aroylamino and diethoxycarbonyl imino-1,3,4-thiadiazole compounds (3a-e, 4a-e, 5a-c) were synthesized via the reaction of 2-amino-1,3,4-thiadiazole compounds (2a-e) with acetyl chloride or acetic anhydride, benzoyl chloride or benzoic anhydride and ethyl chloroformate, respectively. The in vitro antitumor activities of some selected compounds were screened and compounds 2a, 2b, 2c, 3a, 3b, 3c, 5a, 5b and 5c were found to be active.

Özet

2-Amino-1,3,4-thiadiazoles compounds (2a-e) were obtained from the reaction of thiosemi carbazide with 2-cyanomethoxyphenoxyacetonitriles (1). Mono acylamino, mono aroylamino and diethoxycarbonyl imino-1,3,4-thiadiazole compounds (3a-e, 4a-e, 5a-c) were synthesized via the reaction of 2-amino-1,3,4-thiadiazole compounds (2a-e) with acetyl chloride or acetic anhydride, benzoyl chloride or benzoic anhydride and ethyl chloroformate, respectively. The in vitro antitumor activities of some selected compounds were screened and compounds 2a, 2b, 2c, 3a, 3b, 3c, 5a, 5b and 5c were found to be active.

🔖

Cite This Article

SANCAK, K., ÜNVER, Y., ER, M. (2007). Synthesis of 2-Acylamino, 2-Aroylamino and Ethoxycarbonyl Imino-1,3,4-thiadiazoles as Antitumor Agents. Turkish Journal of Chemistry, Cilt: 31 - Sayı: 2, 125–134. https://ajindex.com/articles/185059

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (20)

  1. P.C. Unangst, G.P. Shrum, D.T. Dyer and D.J. Schrier, J. Med. Chem. 35, 3691-98 (1992).
  2. M.D. Mullican, M.W. Wilson, D.T. Connor, C.R. Kostlan and D.J. Schrier, J. Med. Chem. 36, 1090-99 (1993).
  3. D.H. Boschelli, D.T. Conner, D.A. Bornemeir, R.D. Dyer, J.A. Kennedy, P.J. Kuipers, G.C. Okonkwo, D.J. Schrier and C.D. Wright, J. Med. Chem. 36, 1802-10 (1993).
  4. D.H. Jones, R. Slack, S. Squires and K.H. Wooldridge, J. Med. Chem. 8, 676-80 (1965).
  5. R.W. Sidwell, R.K. Robins and I.W. Hillyard, Pharmacol. Ther. 6, 123-8 (1978).
  6. J.K. Sughenand T. Yologe, Pharm. Acta Helv. 58, 64-8 (1978).
  7. V.I. Kelarev, R.A. Karakhanov, S.Sh. Gasanvo, G.V. Morozova and K.P. Kuatbekova, J. Org. Chem. USSR, 323-9 (1993).
  8. Sh.A. Shams El-Dine and A.A.B. Hazza, Pharmazie 29, 761-8 (1974).
  9. T. Misato, K. Ko, Y. Honma and E. Taniyama, Jpn Kokai 77 25 028 (1977) [Chem. Abstr. 87, (1977) a]. J.H. Reisdorff, W. Brandes, H. Scheinpflug, B. Homeyer and P. Roessler, Ger. Offen. 2 533 604 (1977) [Chem. Abstr. 88, (1978) 137064b]. G. VanReet, J. Heeres and L. Wals, US Patent 4 160 838 (1979) [Chem. Abstr. 91, (1979) 175361z]. N.S. Habib, S. Abdel-Hamid and M. El-Hawash, Farmaco 44, 1225-32 (1989).
  10. M.R. Stillings, A.P. Welbour and D.S. Walter, J. Med. Chem. 29, 2280-84 (1986).
  11. J.M. Kane, M.A. Staeger, C.R. Dalton, F.P. Miller, M.W. Dubley, A.M.L. Ogden, J.H. Kehne, H.J. Ketteler, T.C. McCloskey, Y. Senyah, P.A. Chmielewski and J.A. Miller, J. Med. Chem. 37, 125-32 (1994).
  12. C. Ainsworth, N.R. Easton, M. Livezey, D.E. Morrison and W.R. Gibson, J. Am. Pharm. Assoc. 5, 383-9 (1962).
  13. C.B. Chapleo, M. Myers, P.L. Myers, J.F. Saville, A.C.B. Smith, M.R. Stillings, I.F. Tulloch, D.S. Walter and A.P. Welbour, J. Med. Chem. 29, 2273-80 (1986).
  14. J.M. Kane, M.W. Dubley, S.M. Sorenson and F.P. Miller, J. Med. Chem. 31, 1253-58 (1988).
  15. R.D. Porsolt, A. Bertinand M. Jalfre, Pharmacodyn. 229, 327-36 (1977).
  16. A. Vamvakides, Ann. Pharm. Fr. 48, 154-59 (1990).
  17. F. Fujikawa, I. Yamashita, T. Seno, M. Sasaki, M. Naito and S. Tsukuma, Yakugaku Zasshi 86 (a) (1966) 864 [Chem. Abstr. 65, (1966) 20086h]. L. Canoira, J. Gonzalo Rodriguez, J.B. Subirats, J.A. Escario, I. Jimenez and A.R. Martinez-Fernandez, Eur. J. Med. Chem. 24, 39-42 (1989).
  18. S. Masanori, O. Toshiharu, T. Hiroko and Y. Yoshitoku, Jpn. Kokai, Tokyo Koho JP 01 31 762 [89 31 762] (1989) [Chem. Abstr. 111, (1989) 153624s]. C. Krishna and K.C. Joshi, P. Chand. Pharmazie 37, 1-12 (1982).
  19. G.T. Seaborg, Science 9, 223 (1984).
  20. S.N. Sawhney, A. Gupta and P.K. Sharma, Indian J.