- Practical and phase transfer-catalyzed synthesis of 6-methoxytryptamine
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A convenient and cost-effective synthesis of 6-methoxytryptamine (1), starting from commercially available phthalimide and 1-bromo-3-chloropropane via PTC N-alkylation, PTC C-alkylation, Japp-Klingemann reaction, hydrolysis, and decarboxylation, has been accomplished with a 44% overall yield. Copyright Taylor & Francis Group, LLC.
- Kuang, Yunyan,Huang, Jian,Chen, Fener
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- Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**
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A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.
- Christmann, Mathias,He, Guoli,List, Benjamin
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p. 13591 - 13596
(2021/05/07)
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- 1-BENZYLSPIRO[PIPERIDINE-4,1′-PYRIDO[3,4-b]indole] ‘co-potentiators’ for minimal function CFTR mutants
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We previously identified a spiro [piperidine-4,1-pyrido [3,4-b]indole] class of co-potentiators that function in synergy with existing CFTR potentiators such as VX-770 or GLGP1837 to restore channel activity of a defined subset of minimal function cystic fibrosis transmembrane conductance regulator (CFTR) mutants. Here, structure-activity studies were conducted to improve their potency over the previously identified compound, 20 (originally termed CP-A01). Targeted synthesis of 37 spiro [piperidine-4,1-pyrido [3,4-b]indoles] was generally accomplished using versatile two or three step reaction protocols with each step having high efficiency. Structure-activity relationship studies established that analog 2i, with 6′-methoxyindole and 2,4,5-trifluorobenzyl substituents, had the greatest potency for activation of N1303K-CFTR, with EC50 ~600 nM representing an ~17-fold improvement over the original compound identified in a small molecule screen.
- Son, Jung-Ho,Phuan, Puay-Wah,Zhu, Jie S.,Lipman, Elena,Cheung, Amy,Tsui, Ka Yi,Tantillo, Dean J.,Verkman, Alan S.,Haggie, Peter M.,Kurth, Mark J.
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- Anti-cancer indole alkaloid compound, preparation method and application thereof
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The invention relates to an anti-cancer compound, which is an indole alkaloid series compound and has a general formula (I). Indole alkaloids have a very good inhibitory effect on multiple solid tumors, such as human breast cancer cells, and further have an inhibitory effect on tumor growth. The compound has an inhibitory effect on the growth of cancer cells, but has no inhibitory effect on the growth of normal cells. The compound can be used alone or in combination with other drugs.
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Paragraph 0039; 0046-0048; 0097; 0104-0106
(2019/06/30)
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- A Desymmetrization-Based Total Synthesis of Reserpine
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Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.
- Park, Jisook,Chen, David Y.-K.
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supporting information
p. 16152 - 16156
(2018/11/23)
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- Indole derivative and uses thereof
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The present invention relates to an indole derivative and uses thereof, wherein the compound and the pharmaceutical composition comprising the compound can be used for antagonizing orexin receptors. The present invention further relates to a method for preparing the compound and the pharmaceutical composition, and uses of the compound and the pharmaceutical composition in treatment or prevention of diseases associated with orexin receptors.
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Paragraph 0204; 0205; 0360; 0361
(2017/09/01)
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- Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors
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Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented.
- Cuny, Gregory D.,Ulyanova, Natalia P.,Patnaik, Debasis,Liu, Ji-Feng,Lin, Xiangjie,Auerbach, Ken,Ray, Soumya S.,Xian, Jun,Glicksman, Marcie A.,Stein, Ross L.,Higgins, Jonathan M.G.
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scheme or table
p. 2015 - 2019
(2012/04/05)
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- Psychotomimetic N-Methyl-N-isopropyltryptamines. Effects of Variation of Aromatic Oxygen Substituents
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Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man.In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues.Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile.The 5-methoxy congeger 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena.Other members of the series exhibited diminished effects.
- Repke, David B.,Grotjahn, Douglas B.,Shulgin, Alexander T.
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p. 892 - 896
(2007/10/02)
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- Vasodilating octahydro-1,12-methano-oxymethano[2,3-a]-indoloquinolizines
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Pentacyclic derivatives of the general formula STR1 wherein R, R1, R2 and R3 are defined hereinbelow are useful as cerebral protectors and vasodilators.
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