250349-75-8

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• 245359-86-8 11-p-phenoxybenzo[b]naphtho[2,3-d]thiophene 

Relevant academic research and scientific papers

Synthesis and PTP1B inhibition of novel 4-aryl-1-oxa-9-thiacyclopenta[b]fluorenes

Novel 4-aryl-1-oxa-9-thiacyclopenta[b]fluorenes were designed, synthesized, and evaluated as inhibitors of the protein tyrosine phosphatase, PTP1B. Compounds 3 (IC50 = 284 nM) and 4 (IC50 = 74 nM), showed nanomolar potency against PTP1B (TRDI(P)YETD(P)YRK as substrate). Compound 4 also lowered insulin in the diabetic ob/ob mouse at a dose of 10 mg/kg/day, po. (C) 2000 Elsevier Science Ltd. All rights reserved.

11-aryl-benzo[B]naphtho[2,3-D]furans and 11-aryl-benzo[B]naphtho[2,3-D]thiophenes useful in the treatment of insulin resistance and hyperglycemia

This invention provides compounds of Formula I having the structure wherein A is hydrogen, halogen, or OH; B and D are each, independently, hydrogen, halogen, CN, alkyl of 1-6 carbon atoms, aryl, aralkyl of 6-12 carbon atoms, nitro, amino or OR; R is hydrogen, alkyl of 1-6 carbon atoms, -COR1, -CH2CO2R1, -CH(R1a)CO2R1, or -SO2R1; R1 and R1a are each, independently, hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms or aryl; E is S, SO, SO2, O; X is hydrogen, halogen, alkyl of 1-6 carbon atoms, CN, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, aryloxy, arylalkoxy of 6-12 carbon atoms, nitro, amino, alkylsulfanyl of 1-6 carbon atoms, arylsulfanyl, pyridylsulfanyl, 2-N,N-dimethylaminoethylsulfanyl, or -OCH2CO2R1b; R1b is hydrogen or alkyl of 1-6 carbon atoms; Y and Z are each, independently, hydrogen or OR2; R2 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl of 6-12 carbon atoms, or -CH2CO2R3; R3 is hydrogen or alkyl of 1-6 carbon atoms; C is hydrogen, halogen or OR4; R4 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R5)W, -C(CH3)2CO2R6, 5-thiazolidine-2,4-dione, -CH(R7)CH2CO2R6, -COR6, PO3(R6)2, or -SO2R6; R5 is hydrogen, alkyl of 1-6 carbon atoms, aralkyl, aryl, CH2(1H-imidazol-4-yl), -CH2(3-1H-indolyl), -CH2CH2(1,3-dioxo-1,3-dihydro-isoindol-2-yl), -CH2CH2(1-oxo-1,3-dihydro-isoindol-2-yl), -CH2(3-pyridyl), or -CH2CO2H; W is -CO2R6, -CONH2, -CONHOH, CN, -CONH(CH2)2CN, 5-tetrazole, -PO3(R6)2, -CH2OH, or -CH2Br, -CONR6CHR7CO2R8, R6 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R7 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; R8 is hydrogen, alkyl of 1-6 carbon atoms, aryl or aralkyl; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.