41505-84-4Relevant academic research and scientific papers
Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds
Abe, Takumi,Shimizu, Haruka,Takada, Shiori,Tanaka, Takahiro,Yoshikawa, Mai,Yamada, Koji
supporting information, p. 1589 - 1592 (2018/03/23)
A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.
New route of benzyne cyclization for synthesis of 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole derivatives avoiding highly toxic aryl hydrazines
Kovacikova, Lucia,Stefek, Milan
, p. 1257 - 1263 (2015/04/27)
A new route for the regioselective synthesis of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole derivatives was developed based on cyclization of 3-chlorophenylimine-N-alkyl-4-piperidones by "the complex bases" of NaNH2 or KNH2. The procedure was performed under variable reaction conditions in inert proton-free solvents, such as THF, dioxane, 1,2-dimethoxyethane, toluene, and xylene, at temperatures varying from 20C to boiling point of the solvent used. Toxic arylhydrazine intermediates occurring in the classical Fischer indole synthesis are avoided.
Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation
Wang, Shengzheng,Wang, Yan,Liu, Wei,Liu, Na,Zhang, Yongqiang,Dong, Guoqiang,Liu, Yang,Li, Zhengang,He, Xiaomeng,Miao, Zhenyuan,Yao, Jianzhong,Li, Jian,Zhang, Wannian,Sheng, Chunquan
, p. 506 - 511 (2014/06/09)
A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.
Constructions of tetrahydro-γ-carboline skeletons via intramolecular oxidative carbon-carbon bond formation of enamines
Lv, Jinglei,Li, Ji,Zhang-Negrerie, Daisy,Shang, Siyun,Gao, Qingzhi,Du, Yunfei,Zhao, Kang
, p. 1929 - 1932 (2013/06/04)
The synthetically and biologically important 4-methyl and 4-methoxy tetrahydro-γ-carboline compounds were readily synthesized in high yields from an aryl amine and a 5-amino-3-oxopentanoate derivative through a series of reactions of enamination, oxidative annulation, deprotection/lactamization and the final reduction reaction of the carbonyl group. The underpinning strategy involves the oxidative C(sp2)-C(sp2) bond formation realized by either Pd(OAc)2/Cu(OAc)2 or a hypervalent iodine reagent.
Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells
Kalin, Jay H.,Butler, Kyle V.,Akimova, Tatiana,Hancock, Wayne W.,Kozikowski, Alan P.
experimental part, p. 639 - 651 (2012/03/11)
Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both β- and γ-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.
PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE DERIVATIVES
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Page/Page column 11, (2011/11/30)
The value of the invention is the application of the cyclization of Schiff-bases of the general formula (3a-i), where R1 - R8 are substituents defined in example 1, whereby R9 = Cl using complex bases of amides of group I of the periodic table (NaNH2, KNH2) from 2.1 - 5 equiv. and alcoholates of group I of the periodic table (t-BuONa, tBuOK) from 0.05 - 2 equiv. with the advantage of application of 3 equiv. of NaNH2 and 0.05 equiv. of t-BuONa, or their mixtures with PEG (m.w. = 500 - 6000), or crown ethers, or catalysts of phase transfer lithium in inert proton-free diluents, such as benzene, cyclohexane, toluene, xylene, 1,2-dimethoxyethane, dioxane, etc., with the advantage of using THF, at a temperature from 20 °C to boiling point of the diluent used, or with the application of organo-metallic bases such as LDA, t-BuLi in inert proton-free diluents at a temperature from -80°C to 25 °C.
Ruthenium-catalyzed γ-carbolinium ion formation from aryl azides; Synthesis of dimebolin
Dong, Huijun,Latka, Regina T.,Driver, Tom G.
, p. 2726 - 2729 (2011/06/28)
A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.
