Discovery of thienopyrimidine-based inhibitors of the human farnesyl pyrophosphate synthase - Parallel synthesis of analogs via a trimethylsilyl ylidene intermediate

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 8, 2013, Pages 2229-2240

  Leung, Chun Yuen ^a   Langille, Adrienne M ^a   Mancuso, John ^a,b   Tsantrizos, Youla S ^a  

^a MCGILL UNIVERSITY   (Canada)

^b Tranzyme Pharma   (Canada)

Author keywords

2 (1 (Trimethylsilyl)ethylidene)malononitrile; Farnesyl pyrophosphate synthase; Modified Gewald synthesis; Thienopyrimidine bisphosphonates

Indexed keywords

(6 PHENYLTHIENO[2,3 D]PYRIMIDIN 4 YLAMINO)METHYLENEBISPHOSPHONIC ACID; (THIENO[2,3 D]PYRIMIDIN 4 YLAMINO)METHYLENEBISPHOSPHONIC ACID; 2 [1 (TRIMETHYLSILYL)ETHYLIDENE]MALONONITRILE; 2 AMINO 4 (TRIMETHYLSILYL)THIOPHENE 3 CARBONITRILE; [[(2 PHENYLTHIENO[2,3 D]PYRIMIDIN 4 YL)AMINO]METHYLENE]DIPHOSPHONIC ACID; [[(5 PHENYLTHIENO[2,3 D]PYRIMIDIN 4 YL)AMINO]METHYLENE]DIPHOSPHONIC ACID; [[[6 (4 TOLYL)THIENO[2,3 D]PYRIMIDIN 4 YL]AMINO]METHYLENE]DIPHOSPHONIC ACID; [[[6 (NAPHTHALEN 2 YL)THIENO[2,3 D]PYRIMIDIN 4 YL]AMINO]METHYLENE]DIPHOSPHONIC ACID; BISPHOSPHONIC ACID DERIVATIVE; ENZYME INHIBITOR; FARNESYL PYROPHOSPHATE SYNTHASE; FARNESYL PYROPHOSPHATE SYNTHASE INHIBITOR; MALONONITRILE; NITRILE; SULFUR; SYNTHETASE; THIENO[2,3 D]PYRIMIDIN 4 AMINE DERIVATIVE; THIENOPYRIMIDINE DERIVATIVE; TRIMETHYLSILYLYLIDENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; IODINATION; IPSO IODODESILYLATION;

CYCLIZATION; ENZYME INHIBITORS; GERANYLTRANSTRANSFERASE; HUMANS; MODELS, MOLECULAR; NITRILES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84875731060     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.006     Document Type: Article

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