Synthesis and SAR of cis-1-Benzoyl-1,2,3,4-tetrahydroquinoline ligands for control of gene expression in ecdysone responsive systems

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 11, 2003, Pages 1943-1946

  Smith, Howard C ^a   Cavanaugh, Caitlin K ^a   Friz, Jennifer L ^a   Thompson, Christine S ^a   Saggers, Jessica A ^a   Michelotti, Enrique L ^b,d   Garcia, Javier ^b   Tice, Colin M ^a,c  

^a RHeoGene   (United States)

^b ROHM AND HAAS COMPANY   (United States)

^c 19034   (United States)

^d Locus Discovery Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZOYL 2 METHYL 4 (PHENYLAMINO) 1,2,3,4 TETRAHYDROQUINOLINE; ECDYSONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AEDES AEGYPTI; ARTICLE; CONTROLLED STUDY; DOWN REGULATION; DRUG SYNTHESIS; GENE EXPRESSION; LIPOPHILICITY; MAMMAL CELL; NONHUMAN; REPORTER GENE; STRUCTURE ACTIVITY RELATION;

AEDES AEGYPTI; MAMMALIA;

EID: 0038056100     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00317-2     Document Type: Article

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21. By contrast, treatment of the trans-diamines 5a-c with one equivalent of a benzoyl chloride, even under carefully controlled conditions, always afforded a mixture of starting diamine, product that was monoacylated on the ring nitrogen and diacylated product. In no case was the product of monoacylation on the exocyclic nitrogen isolated.
22. 3) 3100, 1631, 1311; MS (ESI, +ve ion) m/z 377 (M+1).
23. 50s were calculated from dose response data using a three parameter logistic model.