Synthesis, SAR, and preliminary mechanistic evaluation of novel antiproliferative N 6,5′-bis-ureido- and 5′-carbamoyl- N 6-ureidoadenosine derivatives

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 1008-1019

  Shelton, Jadd R ^a   Cutler, Christopher E ^a   Oliveira, Marcelio ^a   Balzarini, Jan ^b   Peterson, Matt A ^a  

^a N243 Eyring Science Center   (United States)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Anticancer nucleosides; Antiproliferative activity; BMPR1b; N 6,5 Bis ureidoadenosines

Indexed keywords

2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' (METHYLCARBAMOYL) N6 (N BENZYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' (METHYLCARBAMOYL) N6 [N (4 NITROPHENYL)CARBAMOYL]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' (METHYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' (N METHYLCARBAMOYL) N6 (N PHENYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO] N6 (N PHENYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO] N6 (N PROPYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO] N6 [N (4 NITROPHENYL)CARBAMOYL]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 (ETHOXYCARBAMOYL) 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 (N HEXYLCARBAMOYL) 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (3 IODOPHENYL)CARBAMOYL] 5' [(METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (4 IODOPHENYL)CARBAMOYL] 5' [(METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (4 METHOXYPHENYL)CARBAMOYL] 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL N6 (N CYCLOHEXYLCARBAMOYL) 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL N6 [N (4 CHLOROPHENYL)CARBAMOYL] 5' (N METHYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL N6 [N (4 CHLOROPHENYL)CARBAMOYL] 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL N6 [N (4 METHOXYPHENYL)CARBAMOYL] 5' (METHYLCARBAMOYL)ADENOSINE; 2',3' BIS O TERT BUTYLDIMETHYLSILYL N6 ETHOXYCARBONYL 5' (N METHYLCARBAMOYL)ADENOSINE; 5' AZIDO 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 (N BENZYLCARBAMOYL)ADENOSINE; 5' AZIDO 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (4 CHLOROPHENYL)CARBAMOYL]ADENOSINE; 5' AZIDO 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (4 METHOXYPHENYL)CARBAMOYL]ADENOSINE; 5' AZIDO 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY N6 [N (4 NITROPHENYL)CARBAMOYL]ADENOSINE; 5' CARBAMOYL N6 UREIDOADENOSINE DERIVATIVE; ADENOSINE TRIPHOSPHATE; ANTIMITOTIC AGENT; BONE MORPHOGENETIC PROTEIN RECEPTOR 1B; N6 (N BENZYLCARBAMOYL) 2',3' BIS O TERT BUTYLDIMETHYLSILYL 5' DEOXY 5' [(N METHYLCARBAMOYL)AMINO]ADENOSINE; N6,5' BIS UREIDOADENOSINE DERIVATIVE; PROTEIN KINASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ANIMAL CELL; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING SITE; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOSTASIS; DRUG BINDING; DRUG CONFORMATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; HEATING; HUMAN; HUMAN CELL; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

ADENOSINE; ANTINEOPLASTIC AGENTS; BONE MORPHOGENETIC PROTEIN RECEPTORS, TYPE I; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PROTEIN BINDING; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855777370     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.11.043     Document Type: Article

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