메뉴 건너뛰기




Volumn 39, Issue 2, 1996, Pages 614-618

Analogues of 10-deazaaminopterin and 5-alkyl-5,10-dideazaaminopterin with the 4-substituted 1-naphthoyl group in the place of 4-substituted benzoyl

Author keywords

[No Author keywords available]

Indexed keywords

10 DEAZAAMINOPTERIN; 5,10 DIDEAZAAMINOPTERIN; AMINOPTERIN DERIVATIVE; BENZENE DERIVATIVE; EDATREXATE; METHOTREXATE; N [4 [2 (2,4 DIAMINO 6 PTERIDINYL)ETHYL] 1 NAPHTHOYL]GLUTAMIC ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030031241     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9506940     Document Type: Article
Times cited : (17)

References (22)
  • 1
    • 0002854768 scopus 로고
    • The Biochemistry of Folates
    • Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: Orlando, FL
    • Kisliuk, R. L. The Biochemistry of Folates in Folate Antagonists as Therapeutic Agents; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: Orlando, FL, 1984; Vol. 1, pp 1-68.
    • (1984) Folate Antagonists as Therapeutic Agents , vol.1 , pp. 1-68
    • Kisliuk, R.L.1
  • 3
    • 0343569440 scopus 로고
    • Folate Antimetabolites Inhibitory to de novo Purine Synthesis
    • Muggia, F. M., Ed.; Kluwer Academic Publishers: Boston, MA
    • Moran, R. G. Folate Antimetabolites Inhibitory to de novo Purine Synthesis. In New Drugs, Concepts and Results in Cancer Chemotherapy; Muggia, F. M., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; pp 60-87.
    • (1992) New Drugs, Concepts and Results in Cancer Chemotherapy , pp. 60-87
    • Moran, R.G.1
  • 4
    • 0345338969 scopus 로고
    • Experimental Cancer Chemotherapy with Folate Antagonists
    • Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: Orlando, FL
    • Hutchinson, D. J.; Schmid, F. A. Experimental Cancer Chemotherapy with Folate Antagonists. In Folate Antagonists as Therapeutic Agents; Sirotnak, F. M., Burchall, J. J., Ensminger, W. B., Montgomery, J. A., Eds.; Academic Press: Orlando, FL, 1984; Vol. 2, pp 1-22.
    • (1984) Folate Antagonists as Therapeutic Agents , vol.2 , pp. 1-22
    • Hutchinson, D.J.1    Schmid, F.A.2
  • 6
    • 0025114169 scopus 로고
    • Preferential Selection during Therapy in vivo by Edatrexate Compared to Methotrexate of Resistant L1210 Cell Variants with Decreased Folylpolyglutamate Synthetase Activity
    • Rumberger, B. G.; Schmid, F. A.; Otter, G. M.; Sirotnak, F. M. Preferential Selection During Therapy in vivo by Edatrexate Compared to Methotrexate of Resistant L1210 Cell Variants with Decreased Folylpolyglutamate Synthetase Activity. Cancer Commun. 1990, 9, 305-310.
    • (1990) Cancer Commun. , vol.9 , pp. 305-310
    • Rumberger, B.G.1    Schmid, F.A.2    Otter, G.M.3    Sirotnak, F.M.4
  • 7
    • 0016812788 scopus 로고
    • Further Evidence for a Basis of Selective Activity and Relative Responsiveness during Antifolate Therapy of Murine Tumors
    • Sirotnak, F. M.; Donsbach, R. C. Further Evidence for a Basis of Selective Activity and Relative Responsiveness during Antifolate Therapy of Murine Tumors. Cancer Res. 1975, 35, 1737-1744.
    • (1975) Cancer Res. , vol.35 , pp. 1737-1744
    • Sirotnak, F.M.1    Donsbach, R.C.2
  • 8
    • 0021328814 scopus 로고
    • New Folate Analogs of the 10-Deaza-aminopterin Series: Basis for Structural Design and Biochemical and Pharmacologic Properties
    • Sirotnak, F. M.; DeGraw J. I.; Moccio, D. M.; Samuels, L. L.; Goutas, L. J. New Folate Analogs of the 10-Deaza-aminopterin Series: Basis for Structural Design and Biochemical and Pharmacologic Properties. Cancer Chemother. Pharmacol. 1984, 12, 18-25.
    • (1984) Cancer Chemother. Pharmacol. , vol.12 , pp. 18-25
    • Sirotnak, F.M.1    DeGraw, J.I.2    Moccio, D.M.3    Samuels, L.L.4    Goutas, L.J.5
  • 9
    • 0021363905 scopus 로고    scopus 로고
    • New Folate Analogs of the 10-Deaza-aminopterin series. Further Evidence for Markedly Increased Antitumor Efficacy Compared with Methotrexate in Ascitic and Solid Murine Tumor Models
    • Sirotnak, F. M.; DeGraw J. I.; Schmid, F. A.; Goutas, L. J.; Moccio, D. M. New Folate Analogs of the 10-Deaza-aminopterin series. Further Evidence for Markedly Increased Antitumor Efficacy Compared with Methotrexate in Ascitic and Solid Murine Tumor Models. Cancer Chemother. Pharmacol. 12, 26-30.
    • Cancer Chemother. Pharmacol. , vol.12 , pp. 26-30
    • Sirotnak, F.M.1    DeGraw, J.I.2    Schmid, F.A.3    Goutas, L.J.4    Moccio, D.M.5
  • 11
    • 0025970198 scopus 로고
    • The Renewed Potential for Folate Antagonists in Comtemporary Cancer Chemotherapy
    • Reviewed by Berman, E. M.; Werbel, L. M. The Renewed Potential for Folate Antagonists in Comtemporary Cancer Chemotherapy. J. Med. Chem. 1991, 34, 479-485.
    • (1991) J. Med. Chem. , vol.34 , pp. 479-485
    • Berman, E.M.1    Werbel, L.M.2
  • 12
    • 0027723626 scopus 로고
    • Studies on Analogues of Classical Antifolates Bearing the Naphthoyl Group in Place of Benzoyl in the Side Chain
    • Piper, J. R.; Johnson, C. A.; Maddry, J. A.; Malik, N. D.; McGuire, J. J.; Otter, G. M.; Sirotnak, F. M. Studies on Analogues of Classical Antifolates Bearing the Naphthoyl Group in Place of Benzoyl in the Side Chain. J. Med. Chem. 1993, 36, 4161-4171.
    • (1993) J. Med. Chem. , vol.36 , pp. 4161-4171
    • Piper, J.R.1    Johnson, C.A.2    Maddry, J.A.3    Malik, N.D.4    McGuire, J.J.5    Otter, G.M.6    Sirotnak, F.M.7
  • 13
    • 0027304579 scopus 로고
    • Synthesis and Antitumor Activity of 10-Propargyl-10-deazaaminopterin
    • DeGraw, J. I.; Colwell, W. T.; Piper, J. R.; Sirotnak, F. M. Synthesis and Antitumor Activity of 10-Propargyl-10-deazaaminopterin. J. Med. Chem. 1993, 36, 2228-2231.
    • (1993) J. Med. Chem. , vol.36 , pp. 2228-2231
    • DeGraw, J.I.1    Colwell, W.T.2    Piper, J.R.3    Sirotnak, F.M.4
  • 14
    • 13344269481 scopus 로고    scopus 로고
    • Analogs of Methotrexate in Rheumatoid Arthritis. 1. 10-Deazaaminopterins Containing Heteroaroyl Replacements for the Benzoate Moiety
    • Submitted for publication
    • DeGraw, J. I.; Colwell, W. T.; Crase, J.; Smith, R. L.; Piper, J. R.; Waud, W. R.; Sirotnak, F. M. Analogs of Methotrexate in Rheumatoid Arthritis. 1. 10-Deazaaminopterins Containing Heteroaroyl Replacements for the Benzoate Moiety. Submitted for publication in J. Med. Chem.
    • J. Med. Chem.
    • DeGraw, J.I.1    Colwell, W.T.2    Crase, J.3    Smith, R.L.4    Piper, J.R.5    Waud, W.R.6    Sirotnak, F.M.7
  • 15
    • 0031048462 scopus 로고    scopus 로고
    • Analogues of Methotrexate in Rheumatoid Arthritis. 2. Effects of 5-Deazaaminopterin and 5,10-Dideazaaminopterin and Analogues on Type II Collagen-Induced Arthritis in Mice
    • Submitted for publication
    • Piper, J. R.; DeGraw, J. I.; Colwell, W. T.; Johnson, C. A.; Smith, R. L.; Waud, W. R.; Sirotnak, F. M. Analogues of Methotrexate in Rheumatoid Arthritis. 2. Effects of 5-Deazaaminopterin and 5,10-Dideazaaminopterin and Analogues on Type II Collagen-Induced Arthritis in Mice. Submitted for publication in J. Med. Chem.
    • J. Med. Chem.
    • Piper, J.R.1    DeGraw, J.I.2    Colwell, W.T.3    Johnson, C.A.4    Smith, R.L.5    Waud, W.R.6    Sirotnak, F.M.7
  • 16
    • 12344339048 scopus 로고
    • The Chemistry of 1-Naphthaleneacetic Acid Derivatives
    • Ogata, Y.; Okano, M.; Kitamura, Y. The Chemistry of 1-Naphthaleneacetic Acid Derivatives. J. Org. Chem. 1951, 16, 1588-1592.
    • (1951) J. Org. Chem. , vol.16 , pp. 1588-1592
    • Ogata, Y.1    Okano, M.2    Kitamura, Y.3
  • 17
    • 13344281524 scopus 로고
    • Cyanine Dyestuffs with a Naphthalene Nucleus in the Polymethine Chain
    • Kiprianov, A. I.; Shulezhko, A. A. Cyanine Dyestuffs with a Naphthalene Nucleus in the Polymethine Chain. Zh. Org. Khim. (Engl. Transl.) 1966, 2, 1820-1823; Chem. Abstr. 1967, 66, 47297e.
    • (1966) Zh. Org. Khim. (Engl. Transl.) , vol.2 , pp. 1820-1823
    • Kiprianov, A.I.1    Shulezhko, A.A.2
  • 18
    • 13344260504 scopus 로고
    • Kiprianov, A. I.; Shulezhko, A. A. Cyanine Dyestuffs with a Naphthalene Nucleus in the Polymethine Chain. Zh. Org. Khim. (Engl. Transl.) 1966, 2, 1820-1823; Chem. Abstr. 1967, 66, 47297e.
    • (1967) Chem. Abstr. , vol.66
  • 19
    • 0026674646 scopus 로고
    • Synthesis and Antifolate Evaluation of 10-Ethyl-5-methyl-5,10-dideazaaminopterin and an Alternative Synthesis of 10-Ethyl-10-deazaaminopterin (Edatrexate)
    • Piper, J. R.; Johnson, C. A.; Otter, G. M.; Sirotnak, F. M. Synthesis and Antifolate Evaluation of 10-Ethyl-5-methyl-5,10-dideazaaminopterin and an Alternative Synthesis of 10-Ethyl-10-deazaaminopterin (Edatrexate). J. Med. Chem. 1992, 35, 3002-3006.
    • (1992) J. Med. Chem. , vol.35 , pp. 3002-3006
    • Piper, J.R.1    Johnson, C.A.2    Otter, G.M.3    Sirotnak, F.M.4
  • 20
    • 0021813844 scopus 로고
    • Synthesis of the Antileukemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin
    • Taylor, E. C.; Harrington, P. J.; Fletcher, S. R.; Beardsley, G. P.; Moran, R. G. Synthesis of the Antileukemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin. J. Med. Chem. 1985, 28, 914-921.
    • (1985) J. Med. Chem. , vol.28 , pp. 914-921
    • Taylor, E.C.1    Harrington, P.J.2    Fletcher, S.R.3    Beardsley, G.P.4    Moran, R.G.5
  • 21
    • 0017405215 scopus 로고
    • Preparation of 6-(Bromomethyl)-2,4-pteridinediamine Hydrobromide and its Use in Improved Syntheses of Methotrexate and Related Compounds
    • Piper, J. R.; Montgomery, J. A. Preparation of 6-(Bromomethyl)-2,4-pteridinediamine Hydrobromide and its Use in Improved Syntheses of Methotrexate and Related Compounds. J. Org. Chem. 1977, 42, 208-211.
    • (1977) J. Org. Chem. , vol.42 , pp. 208-211
    • Piper, J.R.1    Montgomery, J.A.2
  • 22
    • 0029129850 scopus 로고
    • Further Evaluation of 5-Alkyl-5-deaza Antifolates. 5-Propyl- and 5-Butyl-5-deaza Analogues of Aminopterin and Methotrexate
    • Piper, J. R.; Ramamurthy, B.; Johnson, C. A.; Maddry, J. A.; Otter, G. M.; Sirotnak, F. M. Further Evaluation of 5-Alkyl-5-deaza Antifolates. 5-Propyl- and 5-Butyl-5-deaza Analogues of Aminopterin and Methotrexate. J. Heterocycl. Chem. 1995, 32, 1205-1212.
    • (1995) J. Heterocycl. Chem. , vol.32 , pp. 1205-1212
    • Piper, J.R.1    Ramamurthy, B.2    Johnson, C.A.3    Maddry, J.A.4    Otter, G.M.5    Sirotnak, F.M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.