- SIMPLE SYNTHESES OF LESPEDAMINE AND 5-BROMO-N,N-DIMETHYLTRYPTAMINE BASED ON 1-HYDROXYINDOLE CHEMISTRY
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Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1-hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.
- Somei, Masanori,Kobayashi, Kensuke,Tanii, Keiko,Mochizuki, Toshihiko,Kawada, Yumiko,Fukui, Yoshikazu
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- Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols
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Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).
- Biswas, Nandita,Sharma, Rahul,Srimani, Dipankar
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supporting information
p. 2902 - 2910
(2020/06/03)
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- Indole derivatives and its application on the medicament
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The invention provides indole derivatives or stereisomers, tautomers, nitrogen oxides, solvate, metabolic products, pharmaceutically acceptable salts or prodrugs thereof for treating the alzheimer disease. The invention further discloses a pharmaceutical composition containing the compounds and a method of using the compounds or the pharmaceutical composition thereof to treat the alzheimer disease.
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Paragraph 0224-0227; 0337; 0339-0342
(2019/03/28)
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- Marine AChE inhibitors isolated from Geodia barretti: Natural compounds and their synthetic analogs
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Barettin, 8,9-dihydrobarettin, bromoconicamin and a novel brominated marine indole were isolated from the boreal sponge Geodia barretti collected off the Norwegian coast. The compounds were evaluated as inhibitors of electric eel acetylcholinesterase. Barettin and 8,9-dihydrobarettin displayed significant inhibition of the enzyme, with inhibition constants (Ki) of 29 and 19 μM respectively towards acetylcholinesterase via a reversible noncompetitive mechanism. These activities are comparable to those of several other natural acetylcholinesterase inhibitors of marine origin. Bromoconicamin was less potent against acetylcholinesterase, and the novel compound was inactive. Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure-activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands for the acetylcholinesterase active site. The four natural compounds were also analysed for their butyrylcholinesterase inhibitory activity in addition and shown to display comparable activities. The study illustrates how both barettin and 8,9-dihydrobarettin display additional bioactivities which may help to explain their biological role in the producing organism. The findings also provide new insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.
- Olsen, Elisabeth K.,Hansen, Espen,Moodie, Lindon W. K.,Isaksson, Johan,Sep?i?, Kristina,Cergolj, Marija,Svenson, Johan,Andersen, Jeanette H.
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p. 1629 - 1640
(2016/02/09)
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- Tryptamine derivatives as novel non-nucleosidic inhibitors against hepatitis B virus
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A series of tryptamine derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in the HepG2.2.15 cell line. The preliminary SAR was discussed. Compounds 2e and 4a showed potent antiviral activity (IC50 = 0.4 and 50 = 40.6 and >25 μM, respectively).
- Qu, Shi-Jin,Wang, Gui-Feng,Duan, Wen-Hu,Yao, Shan-Yan,Zuo, Jian-Ping,Tan, Chang-Heng,Zhu, Da-Yuan
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scheme or table
p. 3120 - 3127
(2011/06/24)
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- ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN
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An enantioselective process for preparing zolmitriptan, (S)-4-{[3-[2-(dimethylamine)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone), by asymmetric hydrogenation of (Z)-2-(acetylamino)-3-{[3-N,N-(dimethylamine)ethyl)-1H-indol-5-yl]-2-propenoic acid methyl ester in the presence of hydrogen and an enantioselective chiral phosphine transition metal catalyst.
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Page/Page column 6-7
(2010/09/05)
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- Method to Use Compositions Having Antidepressant Anxiolytic and Other Neurological Activity and Compositions of Matter
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The sponges were collected from a variety of locations in the Florida Keys and separated based on morphology and color. The samples were identified as three species, two of which are well known: V. rigida (Esper, 1794) (order Verongida, family Aplysinidae) and S. aurea (Hyatt, 1875) (order Dictyoceratida, family Thorectidae), and a third S. cerebriformis (Duchassaing and Michelotti, 1864), is less common and separated based on subtle differences of morphology and coloration, from the other two species. Several compounds were isolated and were evaluated in established animal models predictive of neurological related drug function, namely, the rodent FST and the chick anxiety-depression model.
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- SYNTHESIS METHODS AND INTERMEDIATES FOR THE MANUFACTURE OF RIZATRIPTAN
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The invention relates to a process for the manufacture of an 1,2,4-triazol-1-yl compound of the formula [A], or a salt thereof, wherein each of R3 and R4 is hydrogen or lower alkyl, said process comprising reacting a hydrazine compound of the formula [B] wherein R is hydrogen or acyl, R2 is hydrogen or a protecting group, are hydrogen or lower alkyl, and R6 is hydrogen or COOR7, or a salt thereof, with a 1,2,4-triazolyl forming reagent. In addition, novel intermediates for the synthesis of the anti-migraine agent Rizatriptan and methods for their synthesis are presented.
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Page/Page column 34
(2010/02/13)
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- SYNTHESIS OF AMINES AND INTERMEDIATES FOR THE SYNTHESIS THEREOF
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The invention relates in a first embodiment to a method for the manufacture of esters of the formula (I), or especially of amides of the formula (II), wherein the symbols have the meanings given in the specification, as well as other intermediates and compounds useful in the synthesis of tryptamines and other substances mentioned in the title. The synthesis methods and intermediates are useful in the synthesis of pharmaceuticals.
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- 5-CYCLO INDOLE COMPOUNDS AS 5-HT1D RECEPTOR LIGANDS
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Described herein are compounds selective for a 5-HT1D-like receptor, which have general formula (I), wherein A is selected from a six-membered, non-aromatic, optionally substituted carbocycle and a six-membered, non-aromatic, optionally substituted heterocycle having one or two heteroatoms selected from O, S, SO, SO2 and NR; R is selected from H and OH; n is 0 or 1 as permitted by chemical structure; R is selected from CRRCH2NRR or a group of formula (II), (III) or (IV); R is selected from H and benzoyl; R is selected from H, loweralkyl, benzyl, loweralkylcarbonyl, loweralkylaminocarbonyl; loweralkylaminothiocarbonyl, loweralkanoyl, loweralkylaminoimide and loweralkoxy-substituted loweralkylene; R and R are independently selected from H, loweralkoxy and hydroxy; R and R are independently selected from H and loweralkyl or R and R form an alkylene bridge which, together with the nitrogen atom to which they are attached, creates an optionally substituted 3- to 6-membered ring; ----- denotes a single or double bond; and R, R and R are independently selected from H and loweralkyl. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT1D-like receptor is implicated, such as migraine.
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Page/Page column 13
(2008/06/13)
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- A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and β-carbolines
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(matrix presented) Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. β-Carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R1. Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R2. If X = Br, Suzuki coupling can be used to introduce R3. After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition.
- Wu, Tom Y. H.,Schulte, Peter G.
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p. 4033 - 4035
(2007/10/03)
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- Process for the production of indole derivatives
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The invention provides a process for the production of a compound of formula I, which comprises reacting a compound of formula II with a compound of formula III, in the presence of a strong base and a palladium(0) catalyst, at an elevated temperature, in a solvent which does not adversely affect the reaction. Compounds of formula I may be further processed to compounds of formula V, which are useful in the treatment of inter alia migraine.
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- 5-Bicycloindole compounds
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Disclosed herein are compounds selective for a 5-HT 1D receptor, the compounds having the general formula (I): STR1Also disclosed is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT 1D receptor is indicated such as migrane.
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- 5-CYCLO INDOLE COMPOUNDS
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Described herein are compounds selective for a 5-HT 1D-like receptor, which have the general formula: STR1 wherein A is selected from a six-membered, non-aromatic, optionally substituted carbocycle and a six-membered, non-aromatic, optionally substituted heterocycle having one or two heteroatoms selected from O, S, SO, SO 2 and N 4 ; R 1 is selected from H and OH;n is 0 or 1 as permited by chemical structure;R 2 is selected from CR 5 CR 6 CH. sub.2 NR 7 R 8 or a group of formula II, III or IV: STR2 R. sup.3 is selected from H and benzoyl; R 4 is selected from H, loweralkyl, benzyl, loweralkylcarbonyl, loweralkylaminocarbonyl, loweralkylaminothiocarbonyl, loweralkanoyl, loweralkylaminoimide and loweralkoxy-substituted loweralkylene; R 5 and R. sup.6 are independently selected from H, loweralkoxy and hydroxy;R 7 and R. sup.8 are independently selected from H and loweralkyl or R 7 and R. sup.8 form an alkylene bridge which, together with the nitrogen atom to which they are attached, creates an optionally substituted 3-to 6-membered ring; denotes a single or double bond; andR. sup.9, R. sup.10 and R. sup.11 are independently selected from H and loweralkyl. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of a 5-HT 1D-like receptor is implicated, such as migraine.
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