N9-substituted 2,4-diaminoquinazolines: Synthesis and biological evaluation of lipophilic inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase (Journal of Medicinal Chemistry (2008) 51, (6196) DOI: 10.1021/jm800694g);N9-substituted 2,4-diaminoquinazolines: Synthesis and biological evaluation of lipophilic inhibitors of Pneumocystis carinii and Toxoplasma gondii dihydrofolate reductase

Journal of Medicinal Chemistry

Volumn 51, Issue 19, 2008, Pages 6195-6200

  Gangjee, Aleem ^a   Adair, Ona O ^a   Pagley, Michelle ^a   Queener, Sherry F ^b  

^a DUQUESNE UNIVERSITY   (United States)

^b INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIAMINO 6 [N (2,5 DIMETHOXYBENZYL) N ETHYLAMINO]QUINAZOLINE; DIHYDROFOLATE REDUCTASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; NONHUMAN; PNEUMOCYSTIS CARINII; TOXOPLASMA GONDII;

EID: 53549117494     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900938h     Document Type: Erratum

References (28)

1. Seage, G. R.; Losina, E.; Goldie, S. J.; Paltiel, A. D.; Kimmel, A. D.; Freedberg, K. A. The Relationship of Preventable Opportunistic Infections, HIV-1 RNA, and CD4 Cell Counts to Chronic Mortality. JAIDS, J. Acquired Immune Defic. Syndr. 2002, 30, 421-428.
2. Klepser, M. E.; Klepser, T. B. Drug Treatment of HIV-Related Opportunistic Infections. Drugs 1997, 53, 40-73.
3. DeClercq, E. Toward Improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections. J. Med. Chem. 1995, 38, 2491-2517.
4. Allegra, C. J.; Kovacs, J. A.; Drake, J. C.; Swan, J. C.; Chabner, B. A.; Masur, H. Activity of Antifolates against Pneumocystis carinii Dihydrofolate Reductase and Identification of a Potent New Agent. J. Exp. Med. 1987, 165, 926-931.
5. Fischl, M. A.; Dickinson, G. M.; LaVoie, L. Safety and Efficacy of Sulfamethoxazole and Trimethoprim Chemoprophylaxis for Pneumocystis carinii Pneumonia in AIDS. J. Am. Med. Assoc. 1988, 259, 1185-1189.
6. Roudier, C.; Caumes, E.; Rogeauz, O.; Bricaire, F.; Gentilini, M. Adverse Cutaneous Reactions to Trimethoprim-Sulfamethoxazole in Patients with the Acquired Immunodeficiency Syndrome and Pneumocystis carinii Pneumonia. Arch. Dermatol. 1994, 30, 1383-1386.
7. Allegra, C. J.; Chabner, B. A.; Tuazon, C. U.; Ogata-Arakaki, D.; Baird, B.; Drake, J. C.; Simmons, J. T.; Lack, E. E.; Shelhamer, J. H.; Balis, F.; Walker, R.; Kovacs, J. A.; Lane, H. C.; Masur, H. Trimetrexate for the Treatment of Pneumocystis carinii Pneumonia in Patients with the Acquired Immunodeficiency Syndrome. N. Engl. J. Med. 1987, 317, 978-985.
8. Masur, H.; Polis, M. A.; Tuazon, C. V.; Ogota-Arakaki, D.; Kovacs, J. A.; Katz, D.; Hilt, D.; Simmons, T.; Feuerstein, I.; Lundgren, B.; Lane, H. C.; Chabner, B. A.; Allegra, C. J. Salvage Trial of Trimetrexate-Leucovorin for the Treatment of Cerebral Toxoplasmosis. J. Infect. Dis. 1993, 167, 1422-1426.
9. Gangjee, A.; Vasudevan, A; Queener, S. F.; Kisliuk, R. L. 2,4-Diamino-5-Deaza-6-Substituted Pyrido[2,3-d]pyrimidine Antifolates as Potent and Selective Nonclassical Inhibitors of Dihydrofolate Reductases. J. Med. Chem. 1996, 39, 1438-1446.
10. News. FDA Approves Trimetrexate as Second line Therapy of Pneumocystis carinii Pneumonia Am. J. Hosp. Pharm. 1994, 51, 591-592.
11. Gangjee, A.; Zeng, Y.; McGuire, J. J.; Kisliuk, R. L. Synthesis of N-[4-[1-Ethyl-2-(2,4-Diaminofuro[2,3-d]pyridimin-5-yl)-ethyl] benzoyl]-L-glutamic Acid as an Antifolate. J. Med. Chem. 2002, 45, 1942-1948.
12. Gangjee, A.; Adair, O.; Queener, S. F. Synthesis of 2,4-Diamino-6- (thioarylmethyl)pyrido[2,3-d]pyrimidines as Dihydrofolate Reductase Inhibitors. Bioorg. Med. Chem. 2001, 9, 2929-2935.
13. Gangjee, A.; Yu, J.; McGuire, J. J.; Cody, V.; Galitsky, N.; Kisliuk, R. L.; Queener, S. F. Design, Synthesis and X-ray Crystal Structure of a Potent Dual Inhibitor of Thymidylate Synthase and Dihydrofolate Reductase as an Antitumor Agent. J. Med. Chem. 2000, 43, 3837-3851.
14. Gangjee, A.; Zeng, Y.; McGuire, J. J.; Kisliuk, R. L. Effect of C-9 Methyl Substitution and C8-C9 Conformational Restriction on Antifolate and Antitumor Activity of Classical 5-Substituted 2,4-Diaminofuro[2,3-d] pyrimidines. J. Med. Chem. 2000, 43, 3125-3133.
15. Gangjee, A.; Adair, O.; Queener, S. F. Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase Inhibitors and Antitumor Agents: Synthesis and Biological Activities of 2,4-Diamino-5-methyl-6-[(monosubstituted anilino)methyl]-pyrido[2,3-d]pyrimidines. J. Med. Chem. 1999, 42, 2447-2455.
16. Gangjee, A.; Zhu, Y.; Queener, S. F. 6-Substituted 2,4-Diaminopyrido[3,2- d]pyrimidine Analogues of Piritrexim as Inhibitors of Dihydrofolate Reductase from Rat Liver, Pneumocystis carinii, and Toxoplasma gondii and as Antitumor Agents. J. Med. Chem. 1998, 41, 4533-4541.
17. Rosowsky, A.; Papoulis, A. T.; Forsch, R. A.; Queener, S. F. Synthesis and Antiparasitic and Antitumor Activity of 2,4-Diamino-6-(Arylmethyl)-5,6,7,8- Tetrahydroquinazoline Analogues of Piritrexim. J. Med. Chem. 1999, 42, 1007-1017.
18. Robson, C.; Meek, M. A.; Grunwaldt, J.-D.; Lambert, P. A.; Queener, S. F.; Schmidt, D.; Griffin, R. J. Nonclassical 2,4-Diamino-5-aryl-6- ethylpyrimidine Antifolates: Activity as Inhibitors of Dihydrofolate Reductase from Pneumocystis carinii and Toxoplasma gondii and as Antitumor Agents. J. Med. Chem. 1997, 40, 3040-3048.
19. Stevens, M. F. G.; Phillip, K. S.; Rathbone, D. L.; O'Shea, D. M.; Queener, S. F.; Schwalbe, C. H.; Lambert, P. A. Structural Studies on Bioactive Compounds. 28. Selective Activity of Triazenyl-Substituted Pyrimethamine Derivatives against Pneumocystis carinii Dihydrofolate Reductase. J. Med. Chem. 1997, 40, 1886-1893.
20. Piper, J. R.; Ramamurthy, B.; Johnson, C. A.; Otter, G. M.; Sirotnak, F. M. Analogues of 10-Deazaaminopterin and 5-Alkyl-5,10-dideazaaminopterin with the 4-Substituted 1-Naphthoyl Group in the Place of 4-Substituted Benzoyl. J. Med. Chem. 1996, 39, 614-618.
21. Kuyper, L. F.; Baccanari, D. P.; Jones, M. L.; Hunter, R. N.; Tansik, R. L.; Joyner, S. S.; Boytos, C. M.; Rudolph, S. K.; Knick, B.; Wilson, H. R.; Caddell, J. M.; Friedman, H. S.; Comley, J. C. W.; Stables, J. N. High-Affinity Inhibitors of Dihydrofolate Reductase: Antimicrobial and Anticancer Activities of 7,8-Dialkyl-1,3-diaminopyrrolo[3,2-f]quinazolines with Small Molecular Size. J. Med. Chem. 1996, 39, 892-903.
22. Kovacs, J. A.; Allegra, C. J.; Swan, J. C.; Parillo, J. E.; Chabner, B. A.; Masur, H. Potent Antipneumocystis and Antitoxoplasma Activities of Piritrexim, a Lipid Soluble Antifolate. Antimicrob. Agents Chemother. 1988, 32, 430-433.
23. Gangjee, A.; Vidwans, A. P.; Vasudevan, A.; Queener, S. F.; Kisliuk, R. L.; Cody, V.; Li, R.; Galitsky, N.; Luft, J. R.; Pangborn, W. Structure-Based Design and Synthesis of Lipophilic 2,4-Diamino-6-Substituted Quinazolines and Their Evaluation as Inhibitors of Dihydrofolate Reductases and Potential Antitumor Agents. J. Med. Chem. 1998, 41, 3426-3434.
24. Cody, V.; Wojtczak, A.; Kalman, T. I.; Friesheim, J. H.; Blakley, R. L. Conformational Analysis of Human Dihydrofolate Reductase Inhibitor Complexes: Crystal Structure Determination of Wild-Type and F31 Mutant Binary and Ternary Inhibitor Complexes. Adv. Exp. Med. Biol. 1993, 338, 481-486.
25. Champness, J. N.; Achari, A.; Ballantine, S. P.; Bryant, P. IK.; Delves, C. J.; Stammers, D. K. The Structure of Pneumocystis carinii Dihydrofolate Reductase to 1.9 A Resolution. Structure 1994, 2, 915-924.
26. Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W.; Queener, S. F.; Gangjee, A. Analysis of Quinazoline and Pyrido[2,3-d]pyrimidine N9-C10 Reversed-bridged Antifolates in Complex with NAPD+ and Pneumocystis carinii Dihydrofolate Reductase. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2002, 58, 1393-1399.
27. Molecular Distance Measurements with SYBYL 6.3; Tripos Associates, Inc.: 1699 S. Hanely Road, Suite 303, St. Louis, MO 63144.
28. Gangjee, A.; Guo, X.; Queener, S. F.; Cody, V.; Galitsky, N.; Luft, J. R.; Pangborn, W. Selective Pneumocystis carinii Dihydrofolate Reductase Inhibitors: Design, Synthesis and Biological Evaluation of New 2,4-Diamino-5-substituted-furo[2,3-d]pyrimidines. J. Med. Chem. 1998, 41, 1263-1271.