229020-86-4Relevant articles and documents
Synthesis and biological evaluation of FICZ analogues as agonists of aryl hydrocarbon receptor
Leisten, Eric D.,Liu, Binkai,Peterson, Richard E.,Ricke, William A.,Tang, Weiping,Vezina, Chad M.,Winston-McPherson, Gabrielle N.,Wu, Hao,Yang, Ka
supporting information, (2020/01/21)
The aryl hydrocarbon receptor (AhR) is a ligand activated transcription factor involved in multiple biological processes including immune cell differentiation, intestinal function and inflammation. Based on the scaffold of naturally occurring AhR ligand 6
SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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, (2016/03/05)
Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or
Concise synthesis of 6-formylindolo[3,2-b]carbazole (FICZ)
Sekine, Daisuke,Okeda, Shota,Hosokawa, Seijiro
supporting information, p. 1932 - 1934 (2015/02/19)
A concise synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a potent ligand of the aryl hydrocarbon receptor (AhR), has been established. The conjugate addition of the enolate derived from indolylacetate 2 to 2-chloro-3-formylindole 3 was accomplished. The following cyclization reaction under the acidic conditions gave the indolo[3,2-b]carbazole skeleton.
Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b ]carbazoles
Shu, Dongxu,Winston-Mcpherson, Gabrielle N.,Song, Wangze,Tang, Weiping
, p. 4162 - 4165 (2013/09/12)
Various diindolylmethanes were prepared from propargylic ethers and substituted indoles via a platinum-catalyzed tandem indole annulation/arylation cascade. The resulting diindolylmethanes could be converted to natural product malassezin by formylation or indolo[3,2-b]carbazoles by cyclization.
Synthesis of metabolites of the Ah receptor ligand 6-formylindolo[3,2-b] carbazole
Wahlstroem, Niklas,Romero, Ivan,Bergman, Jan
, p. 2593 - 2602 (2007/10/03)
Synthesis of the five mono- and di-hydroxylated metabolites of the aryl hydrocarbon receptor high affinity ligand 6-formylindolo[3,2-b]carbazole is described. The structures of the metabolites were unequivocally established as 2-hydroxy-, 8-hydroxy-, 2,10-dihydroxy-, 4,8-dihydroxy- and 2,8- dihydroxyindolo[3,2-b]carbazole-6-carboxaldehyde. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Syntheses of 6-substituted indolo[3,2-b]carbazoles, including 6- formylindolo[3,2-b]carbazole, an extremely efficient ligand for the TCDD (Ah) receptor
Tholander, Joakim,Bergman, Jan
, p. 6243 - 6260 (2007/10/03)
A number of 6-substituted indolo[3,2-b]carbazoles have been synthesized using 2,3-diindolylmethane 5 as a crucial precursor. Most notably, 6- formylindolo[3,2-b]carbazole 3 has been synthesized, and thereby a previously assigned structure has been confirmed. 6-Formylindolo[3,2-b]carbazole 3 is an extremely efficient ligand for the TCDD (Ah) receptor. A much improved synthesis of 2,3-diindolylmethane 5 has also been developed.