Synthesis and reactions of some new heterocyclic carbohydrazides and related compounds as potential anticancer agents

Molecules

Volumn 8, Issue 10, 2003, Pages 744-755

  Mansour, Abdel Kader ^a   Eid, Mohga M ^a   Khalil, Nasser S A M ^b  

^a CAIRO UNIVERSITY   (Egypt)

^b Agricultural Research Center   (Egypt)

Author keywords

2 Pyrazolines; Carbohydrazides; Pyrazoles; Synthesis

Indexed keywords

2 (1,3,4 TRIPHENYLPYRAZOL 5 YL) 5 PHENYL 1,3,4 OXADIAZOLE; 2 (5 BENZOYLAMINO 1,3,4 TRIPHENYL 2 PYRAZOLIN 5 YL) 1,3,4 OXADIAZOLE 5(4H) THIONE; 2 [5 BENZOYLAMINO 1,3 DIPHENYL 4 (2 METHOXYPHENYL) 2 PYRAZOLIN 5 YL] 1,3,4 OXADIAZOLE 5(4H) THIONE; 5 BENZOYLAMINO 1,3 DIPHENYL 4 (2 METHOXYPHENYL) 2 PYRAZOLINE 5 CARBOHYDRAZIDE; 5 BENZOYLAMINO 1,3,4 TRIPHENYL 2 PYRAZOLINE 5 CARBOHYDRAZIDE; ANTINEOPLASTIC AGENT; HYDRAZIDE DERIVATIVE; N (2 HYDROXYBENZYLIDENE) 1,3 DIPHENYL 4 (2 METHOXYPHENYL)PYRAZOLE 5 CARBOHYDRAZIDE; N (2 HYDROXYBENZYLIDENE) 1,3,4 TRIPHENYLPYRAZOLE 5 CARBOHYDRAZIDE; N (4 METHOXYBENZYLIDENE) 1,3 DIPHENYL 4 (2 METHOXYPHENYL)PYRAZOLE 5 CARBOHYDRAZIDE; N (4 METHOXYBENZYLIDENE) 1,3,4 TRIPHENYLPYRAZOLE 5 CARBOHYDRAZIDE; N (4 METHYLBENZYLIDENE) 1,3,4 TRIPHENYLPYRAZOLE 5 CARBOHYDRAZIDE; N (5,6 DIPHENYL 1,2,4 TRIAZIN 3 YL) 5 BENZOYLAMINO 1,3 DIPHENYL 4 (2 METHOXYPHENYL) 2 PYRAZOLINE 5 CARBOHYDRAZIDE; N (5,6 DIPHENYL 1,2,4 TRIAZIN 3 YL) 5 BENZOYLAMINO 1,3,4 TRIPHENYL 2 PYRAZOLINE 5 CARBOHYDRAZIDE; N (N PHENYLTHIOCARBAMOYL) 5 BENZOYLAMINO 1,3 DIPHENYL 4 (2 METHOXYPHENYL) 2 PYRAZOLIN 5 CARBOHYDRAZIDE; N (N PHENYLTHIOCARBAMOYL) 5 BENZOYLAMINO 1,3 DIPHENYL 4 (2 METHOXYPHENYL) 2 PYRAZOLINE 5 CARBOHYDRAZIDE; N ACETYL 1,3,4 TRIPHENYLPYRAZOLE 5 CARBOHYDRAZIDE; N BENZYLIDENE 1,3 DIPHENYL 4 (2 METHOXYPHENYL)PYRAZOLE 5 CARBOHYDRAZIDE; N BENZYLIDENE 1,3,4 TRIPHENYLPYRAZOLE 5 CARBOHYDRAZIDE; UNCLASSIFIED DRUG;

ACYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROSCOPY; LEUKEMIA CELL; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 3342912990     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/81000744     Document Type: Article

References (27)

1. Polanc, S. Recent Application of Hydrazides and Related Compounds for The Synthesis Of Heterocycles. Targets Heterocycl. Syst. 1999, 3, 33-91 [Chem Abstr. 2000, 133, 237877u].
2. Polanc, S. Recent Application of Hydrazides and Related Compounds for The Synthesis Of Heterocycles. Targets Heterocycl. Syst. 1999, 3, 33-91 [Chem Abstr. 2000, 133, 237877u].
3. Dutta, M. M.; Goswami, B. N.; Kataky, J. C. S. Studies on Biologically Active Heterocycles. Part I. Synthesis and Antifungal Activity of Some New Aroyl Hydrazones and 2,5-Disubstituted-1,3,4-oxadiazoles. J. Heterocyclic Chem. 1986, 23, 793-795 and references cited therein.
4. Yale, H. L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F. M.; Bernstein, J. Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, Their Derivatives and Related Compounds. J. Am. Chem. Soc. 1953, 75, 1933-1942.
5. Bernstein, J.; Lott, W. A.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. V. Isonicotinic Acid Hydrazide (Nydrazid) and Related Compounds. Am. Rev. Tuberc. 1952, 65, 357-364 [Chem. Abstr. 1953, 47, 12623c].
6. Bernstein, J.; Lott, W. A.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. V. Isonicotinic Acid Hydrazide (Nydrazid) and Related Compounds. Am. Rev. Tuberc. 1952, 65, 357-364 [Chem. Abstr. 1953, 47, 12623c].
7. Bernstein, J.; Jambor, W. P.; Lott, W. A.; Pansy, F. E.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. VI. Derivatives of Isoniazid. Am. Rev. Tuberc. 1953, 67, 354-365 [Chem. Abstr. 1954, 48, 3551f].
8. Bernstein, J.; Jambor, W. P.; Lott, W. A.; Pansy, F. E.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. VI. Derivatives of Isoniazid. Am. Rev. Tuberc. 1953, 67, 354-365 [Chem. Abstr. 1954, 48, 3551f].
9. Bernstein, J.; Jambor, W. P.; Lott, W. A.; Pansy, F.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. VII. Heterocyclic Acid Hydrazides and Derivatives. Am. Rev. Tuberc. 1953, 67, 366-375 [Chem. Abstr. 1954, 48, 3551g].
10. Bernstein, J.; Jambor, W. P.; Lott, W. A.; Pansy, F.; Steinberg, B. A.; Yale, H. L. Chemotherapy of Experimental Tuberculosis. VII. Heterocyclic Acid Hydrazides and Derivatives. Am. Rev. Tuberc. 1953, 67, 366-375 [Chem. Abstr. 1954, 48, 3551g].
11. Erman, P. H.; Straub, H. Heterocyclic Hydrazide Derivatives of Monocyclic γ-Lactam Antibiotics. U.S. Pat. US 5,318,963, Jun 7, 1994 [Chem. Abstr. 1995, 122, 55819s].
12. 3 Selective Muscarinic Agonists. Bioorg. Med. Chem. Lett. 1996, 6, 2525-2530 [Chem. Abstr. 1997, 126, 69739k].
13. 3 Selective Muscarinic Agonists. Bioorg. Med. Chem. Lett. 1996, 6, 2525-2530 [Chem. Abstr. 1997, 126, 69739k].
14. Markham, P. N.; Klyachko, E. A.; Crich, D.; Jaber, M. R.; Johnson, M. E.; Mulhearn, D. C.; Neyfakh, A. A. Bactericidal Antimicrobial Methods and Compositions Using Acyl Hydrazides, Oxyamides, and 8- Hydroxyquinolines as Antibiotic Potentiators for Treatment of Gram-Postive Infections. PCT Int. Appl. WO 01 70, 213, Sep 27, 2001
15. Troeberg, L.; Chen, X.; Flaherty, T. M.; Morty, R. E.; Cheng, M.; Hua, H.; Springer, C.; Mc Kerrow, J. H.; Kenyon, G. L.; Lonsdale-Eccles, J. D.; Coetzer, T. H. T.; Cohen, F. E. Chalcone, Acyl Hydrazide, and Related Amides Kill Cultured Trypanosoma Brucei Brucei. Mol. Med. (N.Y.) 2000, 6, 660-669 [Chem. Abstr. 2001, 134, 246896x].
16. Troeberg, L.; Chen, X.; Flaherty, T. M.; Morty, R. E.; Cheng, M.; Hua, H.; Springer, C.; Mc Kerrow, J. H.; Kenyon, G. L.; Lonsdale-Eccles, J. D.; Coetzer, T. H. T.; Cohen, F. E. Chalcone, Acyl Hydrazide, and Related Amides Kill Cultured Trypanosoma Brucei Brucei. Mol. Med. (N.Y.) 2000, 6, 660-669 [Chem. Abstr. 2001, 134, 246896x].
17. Broadhurst, M. J.; Johnson, W. H.; Walter, D. S. Preparation of Hydroxycarbamoylalkylcarboxylic Acid Azacyclic Hydrazides as TNF-α Inhibitors. PTC Int. Appl. WO 00 35,885, Jun 22, 2000 [Chem. Abstr. 2000, 133, 58802u].
18. Milyutin, A. V.; Safonva, N. V.; Chesnokov, V. P.; Nazmetdinov, F. Y.; Voronina, E. V.; Krylora, I. V.; Andreichikov, Y. S.; Kolla, V. E.; Kozhevnikov, Y. V. Synthesis, Properties, and Biological Activity of β- Aroylpyruvylhydrazides of N-Methyl and N-Phenylanthranilic Acids. Khim.-Farm. Zh. 1996, 30, 26-28 [Chem. Abstr. 1996, 125, 185294q].
19. Milyutin, A. V.; Safonva, N. V.; Chesnokov, V. P.; Nazmetdinov, F. Y.; Voronina, E. V.; Krylora, I. V.; Andreichikov, Y. S.; Kolla, V. E.; Kozhevnikov, Y. V. Synthesis, Properties, and Biological Activity of β- Aroylpyruvylhydrazides of N-Methyl and N-Phenylanthranilic Acids. Khim.-Farm. Zh. 1996, 30, 26-28 [Chem. Abstr. 1996, 125, 185294q].
20. Silvestrini, B; Cheng, C. Y. Preparation of 3-Substituted-1-Benzyl-1H- Indoles as Antifertility Agents. U.S. Pat. US 6,001,865 Dec. 14, 1999 [Chem. Abstr. 2000, 132, 22964p].
21. Sengupta, A. K.; Bhatnagar, A. Synthesis and Antimicrobial Screening of [[1-(4-Methyl/chlorophenyl)-1H-tetrazolo-5-yl]thio]acetic Acid [N-Substituted-phenyl)methylene]-hydrazides]. J. Indian Chem. Soc. 1987, LXIV, 616-619.
22. Opie, T. R. Preparation of Benzodioxincarboxylic Acid Hydrazides as insecticides. Eur. Pat. Appl. EP 984,009, Mar 8, 2000 [Chem. Abstr. 2000, 132, 194382p].
23. Tomotaki, Y.; Kamiya, K.; Abe, Y. Deodorant Compositions. PTC Int. Appl. WO 01 62,309, Aug 30, 2001 [Chem. Abstr. 2001, 135, 199698t].
24. Eid, M. M.; Badawy, M. A.; Mansour, A. K. Reactions of 3-Hydrazino-5,6-diphenyl-1,2,4-triazine with 4-Arylidene-2-phenyl-5(4H)- oxazolones and 4-Benzylidene-3-methyl-5(4H)-isoxazolone. J. Heterocyclic Chem. 1998, 25, 1813-1815.
25. Eid, M. M. Reaction of 3-Hydrazino-5,6-diphenyl-1,2,4-triazine with Some Hexoses and Pentoses. J. Carbohydr. Chem. 1999, 10, 461-468.
26. Coutouli-Argyropoulou, E.; Argyropoulos, N. G.; Thessalonikeos, E. 1,3-Dipolar Cycloaddition Reactions of 2-Phenyl-4-arylideneoxazol-5(4H)-ones with Nitrile Imines. A Reinvestigation of The Regiochemistry of The 1,3- Dipolar Cycloaddition Reactions of 2-Phenyl-4-Aryl-ideneoxazol-5(4H)-ones with Nitrile Oxides. J. Chem. Res. 1990, (S) 202-203; (M) 1557.
27. Shawali, A., S.; Fahmi, A.A.; Hassaneen, H. M.; Abdallah, M. A.; Abdelhamid, H. A. 1,3-Dipolar Cycloaddition Rections of Diphenylnitrilimine with Esters of α,β-Didehydro Amino Acids. J. Chem. Res. 1992, (S) 360-361; (M) 2936-2944.