Tumor Targeting with Novel 6-Substituted Pyrrolo [2,3-d] Pyrimidine Antifolates with Heteroatom Bridge Substitutions via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis

Journal of Medicinal Chemistry

Volumn 59, Issue 17, 2016, Pages 7856-7876

  Golani, Lalit K ^a   Wallace Povirk, Adrianne ^b   Deis, Siobhan M ^d   Wong, Jennifer ^d   Ke, Jiyuan ^e   Gu, Xin ^e   Raghavan, Sudhir ^a   Wilson, Mike R ^c   Li, Xinxin ^a   Polin, Lisa ^b,c   De Waal, Parker W ^e   White, Kathryn ^b,c   Kushner, Juiwanna ^b,c   O'Connor, Carrie ^b   Hou, Zhanjun ^b,c   Xu, H Eric ^e,f   Melcher, Karsten ^e   Dann, Charles E ^d   Matherly, Larry H ^b,c   Gangjee, Aleem ^a  

^a DUQUESNE UNIVERSITY   (United States)

^b KARMANOS CANCER INSTITUTE   (United States)

^c WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d INDIANA UNIVERSITY   (United States)

^e VAN ANDEL RESEARCH INSTITUTE   (United States)

^f SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 [2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHOXY]BENZOYL]GLUTAMIC ACID; ANTINEOPLASTIC AGENT; FOLATE RECEPTOR 1; FOLATE RECEPTOR 2; FOLIC ACID ANTAGONIST; LOMETREXOL; METHOTREXATE; PEMETREXED; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; PROTON COUPLED FOLATE TRANSPORTER; PURINE NUCLEOTIDE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; RALTITREXED; UNCLASSIFIED DRUG; [4 [2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHOXY]BENZOYL]GLUTAMIC ACID; [4 [N [2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHYL] 2,2,2 TRIFLUOROACETAMIDO]BENZOYL]GLUTAMIC ACID; [4 [N [2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHYL]ACETAMIDO]BENZOYL]GLUTAMIC ACID; [4 [N [2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHYL]FORMAMIDO]BENZOYL]GLUTAMIC ACID; [4 [[2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHYL]AMINO]BENZOYL]GLUTAMIC ACID; [4 [[2 (2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)ETHYL]THIO]BENZOYL]GLUTAMIC ACID; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER INHIBITION; CHO CELL LINE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; FEMALE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; OVARY TUMOR; PROTEIN SYNTHESIS INHIBITION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; ANIMAL; ANTAGONISTS AND INHIBITORS; BIOSYNTHESIS; CANCER TRANSPLANTATION; CHEMISTRY; DRUG SCREENING; METABOLISM; MOLECULAR DOCKING; SCID MOUSE; SYNTHESIS; TUMOR CELL LINE; XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FOLATE RECEPTOR 1; FOLIC ACID ANTAGONISTS; HETEROGRAFTS; HUMANS; MICE, SCID; MOLECULAR DOCKING SIMULATION; NEOPLASM TRANSPLANTATION; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; PROTON-COUPLED FOLATE TRANSPORTER; PURINE NUCLEOTIDES; PYRIMIDINES; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84986309931     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.6b00594     Document Type: Article

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