70837-63-7Relevant academic research and scientific papers
6-Methoxy-7-benzofuranoxy and 6-methoxy-7-indolyloxy analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a potent and selective α1D-adrenoceptor antagonist
Fumagalli, Laura,Pallavicini, Marco,Budriesi, Roberta,Bolchi, Cristiano,Canovi, Mara,Chiarini, Alberto,Chiodini, Giuseppe,Gobbi, Marco,Laurino, Paola,Micucci, Matteo,Straniero, Valentina,Valoti, Ermanno
, p. 6402 - 6412 (2013/09/23)
Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, α1-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclohexane, or especially by ortho,meta-fused benzene preferentially elicits α1D-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho heterodisubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest α1D-AR antagonist affinity (pA2 9.58) with significant α1D/ α1A and α1D/α1B selectivity. In addition, compared both to α1D-AR antagonists structurally related to 1 and to the well-known α1D-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral α1-AR antagonist behavior.
Iridium-catalyzed C-H borylation-based synthesis of natural indolequinones
Wang, Christy,Sperry, Jonathan
experimental part, p. 2584 - 2587 (2012/05/31)
An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation-hydrolysis to 7-hydroxyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C-H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.
Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum
Fukuyama, Yoshiyasu,Iwatsuki, Chie,Kodama, Mitsuaki,Ochi, Masamitsu,Kataoka, Kumi,Shibata, Kozo
, p. 10007 - 10016 (2007/10/03)
Three new indolequinones, 6-methoxyindole-4,7-quinone (1), 5- methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established
Use of indole derivative for dyeing keratin materials, tinctorial compositions, new compounds and dyeing process
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, (2008/06/13)
Process for dyeing keratin fibers by using derivatives of formula: STR1 where: R1 =H, lower alkyl or SiR11 R12 R13 ; R2 and R3, which may be identical or different, =H, alkyl, carboxyl, alkoxycarbonyl or --COOSiR11 R12 R13 ; R4 to R7, which may be identical or different, =H or an O--Z group, where Z=H, C1 -C20 alkyl, aralkyl, formyl, C2 -C20 acyl, C3 -C20 alkenyl, --SiR11 R12 R13, --P(O)(OR8)2, R8 OSO2 ; or a heterocycle which may contain a P(O)(OR8) or CR9 R10 group; with the reservation that at least two of R4 to R7 denotes OZ or form a ring, and that at least one of R4 or R7 represents OZ; R8 and R9 =H, lower alkyl; R10 =alkoxy, mono- or dialkylamino; R11, R12 and R13, which may be identical or different, are alkyl groups; or their alkali metal, alkaline-earth metal, ammonium and amine salts.
