- SMALL MOLECULES THAT TARGET THE RNA THAT CAUSES ALS
-
Disclosed herein are compounds that selectively bind an expanded transcribed repeat r(G4C2)exp, prevent sequestration of RNA-binding proteins, and inhibit translation of repeat associated non-ATG (RAN) translation responsible for generation of toxic dipeptide repeats underlying diseases such as amyotrophic lateral sclerosis (ALS) and frontotemporal dementia (FTD). The compounds and their pharmaceutical compositions are useful in treating a disease or condition characterized by an expanded G4C2 repeat RNA (r(G4C2)exp), such as ALS and FTD.
- -
-
Paragraph 00707-00709
(2022/04/03)
-
- The structural simplification of lysergic acid as a natural lead for synthesizing novel anti-Alzheimer agents
-
Alzheimer's disease (AD) is a neurodegenerative disorder, projected to be the second leading cause of mortality by 2040. AD is characterized by a progressive impairment of memory leading to dementia and loss of ability to carry out daily functions. In addition to the deficiency of acetylcholine release in synapse, there are other mechanisms explaining the etiology of the disease. The most disputing ones are associated with the accumulation of damaged proteins β-amyloid (Aβ) and hyperphosphorylated tau outside and inside neurons, respectively. Lysergic acid derivatives have been shown to possess promising anti-Alzheimer effect. Moreover, lysergic acid structure encompasses the general structural requirements for acetylcholinesterase inhibition. In this study, sixteen analogues, derived from lysergic acid structure, were synthesized. Heck and Mannich reactions were carried out to 4-bromo indole nucleus to generate potentially active analogues. Some of them were subsequently cyclized by nitromethane and zinc reduction procedures. Some of these compounds showed neuroprotective and anti-inflammatory effects stronger than the currently used anti-Alzheimer drug; donepezil. Some of the synthesized com-pounds showed a noticeable acetylcholinesterase inhibition. Twelve molecular targets attributed with AD etiology were tested versus the synthesized compounds by in silico modeling. Docking scores of modeling were plotted against in vitro activity of the compounds. The one afforded the strongest positive correlation was ULK-1 which has a significant role in autophagy.
- Alzweiri, Muhammed,A. Alsegiani, Amsha,Karaj, Endri,A. Almarghalani, Daniyah,Tabaza, Yahia,A. Shah, Zahoor,Tillekeratne, L.M. Viranga
-
supporting information
(2021/06/26)
-
- Rhodium-Catalyzed Stereoselective Cyclization of 3-Allenylindoles and N-Allenyltryptamines to Functionalized Vinylic Spiroindolenines
-
Herein, we report a highly enantio- and diastereoselective rhodium-catalyzed cyclization of N-allenyltryptamines and 3-allenylindoles to 6-membered spirocyclic indolenines. This allylic addition methodology offers the advantage of using a comparably cheap commercially available ligand with low loadings of an affordable rhodium precursor. The products can be converted into functionalized spirooxindoles and spiroindolines, which are regarded as important building blocks for the synthesis of a lot of natural products with biological activities.
- Becker, Antonia,Breit, Bernhard,Grugel, Christian P.
-
supporting information
p. 3788 - 3792
(2021/05/29)
-
- Photo Click Reaction of Acylsilanes with Indoles
-
Light-mediated coupling of acylsilanes with indoles is reported. This photo click reaction occurs under mild conditions (415 nm) mostly in quantitative yield and provides stable silylated N,O-acetals via light mediated siloxycarbene generation with subsequent indole-N-H insertion. We show that this very efficient and fully atom economic coupling process can be applied to conjugate complex systems, as documented by the clicking of carbohydrates with indole alkaloids. The method is also applicable to the conjugation of polymer chains. The linking acetal moiety can be readily cleaved and it is also shown that wavelength-selective coupling and cleavage with acyl silanes bearing a second photoactive moiety is possible. This is documented by a successful polymerization/depolymerization sequence and by a polymer folding/unfolding process.
- Stuckhardt, Constantin,Studer, Armido,Wissing, Maren
-
supporting information
p. 18605 - 18611
(2021/07/26)
-
- Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity
-
Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3′-ends) in a 2 : 1 stoichiometry.
- Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald
-
p. 1667 - 1679
(2021/03/24)
-
- Visible-light-induced cascade dearomatization cyclization between alkynes and indole-derived bromides: A facile strategy to synthesize spiroindolenines
-
A visible-light-initiated intermolecular dearomatization cyclization cascade reaction between alkynes and indole-derived bromides has been explored. This transformation exhibits a wide substrate scope and significant functional group tolerance, providing an efficient way to access a variety of spiroindolenines under mild conditions. This journal is
- Gao, Xiaoshuang,Yuan, Yao,Xie, Xiaomin,Zhang, Zhaoguo
-
supporting information
p. 14047 - 14050
(2020/11/21)
-
- Novel Preparation of Hemiaminal Derivatives with BPO and N,N-Dimethylamides and Their Synthetic Use for (Aminomethyl)indoles
-
A novel preparation of hemiaminal derivatives bearing both an amide group and a benzoate group was carried out in good yields by the treatment of BPO in N,N-dimethylamides under warming condition at 80 °C or irradiation with a mercury lamp. Further treatment of the obtained hemiaminal derivatives with indoles in 1,1,1,3,3,3-hexafluoro-2-propanol generated the corresponding C–C bonded indoles bearing an amide group in good yields. The formed indoles bearing an amide group were smoothly transformed into the corresponding indoles bearing an aminomethyl group.
- Nakamura, Kohei,Togo, Hideo
-
p. 4713 - 4722
(2020/08/03)
-
- Natural Products for Drug Discovery: Discovery of Gramines as Novel Agents against a Plant Virus
-
Plant viral diseases seriously affect crop yield and quality. The natural product gramine (1) and its simple structural analogues 2-35 were synthesized from indoles, amines, and aldehydes in one step. The antiviral effects of these alkaloids were evaluated systematically. Most of these compounds were found to have higher antiviral effects than commercial ribavirin for the first time. Especially compounds 22, 30, and 31 exhibited significantly higher effects than ningnanmycin, thereby emerging as novel antiviral leads for further optimization. The preliminary implementation indicated that these compounds likely inhibit the assembly of tobacco mosaic virus (TMV) by cross-linking TMV capsid protein. Gramine analogues were also found to have broad-spectrum fungicidal effects. Although gramine has been reported to have influence on germination and development of Erysiphe graminis, these compounds displayed no fungicidal effects against Blumeria graminis f. sp. tritici on wheat in our test. Some of these compounds also exhibited certain insecticidal activities.
- Lu, Aidang,Wang, Tienan,Hui, Hao,Wei, Xiaoye,Cui, Weihao,Zhou, Chunlv,Li, Hongyan,Wang, Ziwen,Guo, Jincheng,Ma, Dejun,Wang, Qingmin
-
p. 2148 - 2156
(2019/03/08)
-
- Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles
-
A highly selective rhodium-catalyzed cyclization of tethered 3-allenylindoles is reported. In a smooth reaction, 1-vinyltetrahydrocarbazoles are obtained in excellent yields and enantioselectivities. Aside from a great functional group tolerance, this method requires neither the Schlenk technique nor the use of anhydrous solvents. Preliminary mechanistic investigations proved that the reaction proceeds via an intermediary formed spiroindolenine which rapidly undergoes an acid-catalyzed stereospecific migration.
- Grugel, Christian P.,Breit, Bernhard
-
supporting information
p. 5798 - 5802
(2019/06/08)
-
- Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines
-
A highly selective rhodium-catalyzed tandem spirocyclization/reduction of 3-allenylindoles is reported. By employing a Hantzsch ester as reductant, vinylic spiroindolines are obtained in excellent yields as well as diastereo- and enantioselectivity. In addition, the reaction's synthetic utility is highlighted by broad functional group compatibility and exemplified by a gram scale reaction with subsequent assorted transformations.
- Grugel, Christian P.,Breit, Bernhard
-
supporting information
p. 9672 - 9676
(2019/12/24)
-
- Directed Aminomethylation of Pyrrole, Indole, and Carbazole with N,N,N′,N′-Tetramethylmethanediamine
-
Catalytic aminomethylation of pyrrole and indole with N,N,N′,N′-tetramethylmethanediamine in the presence of 5 mol % of ZrOCl2·8H2O proceeds selectively at the positions 2, 5 of pyrrole and 1, 3 of indole. Carbazole under the same conditions affords 3-formyl-9-aminomethyl derivative. The reaction in the presence of 5 mol % of K2CO3 occurs as monoaminomethylation: for pyrrole at the position 2, for indole at the position 3, and for carbazole at the nitrogen atom of the substrate. Water-soluble 1,1′-(1H-pyrrole-2,5-diyl)bis(N,N-dimethylmethanamine) exhibits a fungistatic activity with respect to phytopathogenic fungi Rhizoctonia solani.
- Akhmetova,Bikbulatova,Akhmadiev,Yanybin,Boiko,Kunakova,Ibragimov
-
p. 701 - 706
(2018/07/06)
-
- General Synthesis of Unsymmetrical 3,3′-(Aza)diindolylmethane Derivatives
-
Diindolylmethane (DIM) and its derivatives have recently been in the focus of interest due to their significant biological activities, specifically in cancer prevention and therapy. Molecular targets of DIM have been identified, e.g., the immunostimulatory G protein-coupled receptor GPR84. However, most of the reported and investigated DIM derivatives are symmetrical because general methods for obtaining unsymmetrical DIMs have been lacking. To optimize the interaction of DIM derivatives with their protein targets, unsymmetrical substitution is required. In the present study we developed a new, mild and efficient access to unsymmetrically substituted 3,3′-DIMs by reaction of (3-indolylmethyl)trimethylammonium iodides with a wide range of substituted indole derivatives. 7-Azaindole also led to the 3,3′-connected DIM analogue, while 4- and 5-azaindoles reacted at the N1-nitrogen atom as confirmed by X-ray crystallography. The reactions were performed in water without the requirement of a catalyst or other additives. Wide substrate scope, operational simplicity, environmentally benign workup, and high yields are further advantages of the new method. The synthetic protocol proved to be suitable for upscaling to yield gram amounts for pharmacological studies. This procedure will allow the preparation of a broad range of novel, unsymmetrical DIM derivatives to exploit their potential as novel drugs.
- Pillaiyar, Thanigaimalai,Gorska, Ewelina,Schnakenburg, Gregor,Müller, Christa E.
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p. 9902 - 9913
(2018/08/01)
-
- Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)
-
Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.
- See, Cheng Shang,Kitagawa, Mayumi,Liao, Pei-Ju,Lee, Kyung Hee,Wong, Jasmine,Lee, Sang Hyun,Dymock, Brian W.
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p. 344 - 367
(2018/07/25)
-
- Synthesis of N-1-Skatyl Uracil Derivatives
-
N-1 skatyl derivatives were obtained in moderate yields via the reaction of uracil, 5-fluorouracyl, and cytosine with gramine N-oxide or its methyl iodide. Gramine N-oxide was converted into gramine in good yield upon microwave irradiation in DMF solution
- Chernikova,Spirikhin,Yunusov
-
p. 333 - 337
(2017/07/05)
-
- SELECTIVE ANTI-CANCER COMPOUNDS
-
A compound of formula I, wherein the compound of formula I has the structure: wherein R1 to R5, Y, L, Z and X1 to X7 have meanings given in the description, said compounds having utility in the treatment of hyperproliferative disease.
- -
-
Page/Page column 79-80; 104-105
(2017/01/31)
-
- Novel Compounds for Regeneration of Terminally-Differentiated Cells and tissues
-
The present invention discloses novel compounds and their use in medicine. Preferably the compounds are applicable in the therapy of disorders associated with damaged post-mitotic tissues in mammals. The novel compounds are compounds according to formula I wherein - X is O (oxygen) or S (sulphur), - R1 is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted alkyl groups, cycloalkyl groups, alkylcycloalkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, cycloalkylaryl groups and arylcycloalkyl groups, which optionally contain heteroatoms, - R2 is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted C1 - C6 alkyl groups, C1 - C6 alkoxy groups, C1 - C6 alkoxy alkyl groups and C2 - C6 alkenyl groups, - R3 is is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted alkyl groups, cycloalkyl groups, alkylcycloalkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, cycloalkylaryl groups and arylcycloalkyl groups, which optionally contain heteroatoms, - or a stereoisomer, a tautomer, a prodrug or a pharmaceutically acceptable salt thereof.
- -
-
Paragraph 0057
(2015/05/26)
-
- NOVEL COMPOUNDS FOR REGENERATION OF TERMINALLY-DIFFERENTIATED CELLS AND TISSUES
-
The present invention discloses novel compounds and their use in medicine. Preferably the compounds are applicable in the therapy of disorders associated with damaged post-mitotic tissues in mammals. The novel compounds are compounds according to formula I (I) wherein - X is O (oxygen) or S (sulphur), - R1 is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted alkyl groups, cycloalkyl groups, alkylcycloalkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, cycloalkylaryl groups and arylcycloalkyl groups, which optionally contain heteroatoms, - R2 is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted C1 - C6 alkyl groups, C1 – C6 alkoxy groups, C1 – C6 alkoxy alkyl groups and C2 – C6 alkenyl groups, - R3 is a substituent selected from the group consisting of straight-chain (unbranched) or branched, unsubstituted or substituted alkyl groups, cycloalkyl groups, alkylcycloalkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, cycloalkylaryl groups and arylcycloalkyl groups, which optionally contain heteroatoms, - or a stereoisomer, a tautomer, a prodrug or a pharmaceutically acceptable salt thereof.
- -
-
Page/Page column 10; 11
(2015/06/03)
-
- Mild microwave-assisted synthesis of dipyrromethanes and their analogues
-
The Mannich reaction between pyrroles or indoles and Eschenmoser's salt (dimethylmethylideneammonium iodide) forms N,N-dimethylamino-methylated derivatives in good to excellent yields. The reaction is highly regioselective, and for pyrroles both 2-and 3-s
- Xiong, Ruisheng,Borbas, K. Eszter
-
supporting information
p. 484 - 488
(2015/04/14)
-
- Heterocycle-functional gramine analogues: Solvent- and catalyst-free synthesis and their inhibition activities against cell proliferation
-
A series of novel gramine analogues were designed and synthesized via a convenient three-component reaction, and which were evaluated for their inhibition activities against cell proliferation. Their structures were confirmed by satisfactory spectra analyses mainly including 1H NMR, and ESI-MS analyses. The preliminary assays indicated that some of the newly synthesized compounds displayed significantly good inhibition activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) cell lines compared with the control 5-Fluorouracil (5-FU), which might be developed as novel lead scaffold for potential anticancer agents.
- Ke, Shaoyong,Shi, Liqiao,Cao, Xiufang,Yang, Qingyu,Liang, Ying,Yang, Ziwen
-
experimental part
p. 248 - 254
(2012/09/07)
-
- Enantioselective gold-catalyzed allylic alkylation of indoles with ALcohols: An efficient route to functionalized tetrahydrocarbazoles
-
[Chemical equation presented] Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel-Crafts alkylation is described for the first time In the presence of chiral gold complexes. This intramolecular Friedel-Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).
- Bandini, Marco,Eichholzer, Astrid
-
supporting information; experimental part
p. 9533 - 9537
(2010/03/24)
-
- A practical synthesis of indole-based heterocycles using an amidoaluminum-mediated strategy
-
A large number of biologically active compounds consist of an indole scaffolding. Because of this, chemists are continually searching for more efficient means through which to successfully synthesize the required alkaloids. In our recent effort to synthes
- Todd, Robert,Hossain, M. Mahmun
-
experimental part
p. 1846 - 1850
(2010/01/16)
-
- Efficient and practical synthesis of Mannich bases related to gramine mediated by zinc chloride
-
An efficient and practical procedure for the Mannich reaction of secondary amine, formaldehyde, and indole or N-methylindole employing zinc chloride is presented. A series of gramine derivatives were obtained in 58-98% yields at room temperature in EtOH by using this method. Copyright Taylor & Francis Group, LLC.
- Dai, Hong-Guang,Li, Ji-Tai,Li, Tong-Shuang
-
p. 1829 - 1835
(2007/10/03)
-
- Structure-activity relationship study of novel necroptosis inhibitors
-
Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-α. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.
- Teng, Xin,Degterev, Alexei,Jagtap, Prakash,Xing, Xuechao,Choi, Sungwoon,Denu, Regine,Yuan, Junying,Cuny, Gregory D.
-
p. 5039 - 5044
(2007/10/03)
-
- KINASE INHIBITORS
-
The present invention provides kinase inhibitors of Formula (I)
- -
-
Page/Page column 33
(2010/02/07)
-
- A general synthesis of 1-(dialkylaminomethyl)indoles
-
1-(N,N-Dialkylamino)methylindoles are prepared from the corresponding 1-(dialkylaminomethyl)benzotriazoles by treatment with indole and base. The aminoalkylation proceeds in high yield with good regioselectivity.
- Love, Brian E.,Nguyen, Binh T.
-
p. 1123 - 1125
(2007/10/03)
-
- The activation of aminals and aminol ethers by sulfur dioxide and their reactions with electron rich aromatic compounds
-
Reactions of bis(dialkylamino)methanes and ethoxydialkylaminomethanes with nucleophilic aromatic heterocycles in the presence of sulfur dioxide result in the formation of the expected Mannich bases in good yields. Reactions of phenols are similarly activated by sulfur dioxide which lead to improved regioselectivity: in particular the reactions of 2,5-dimethylphenol result in the formation of 2-dialkylaminomethyl-3,6-dimethylphenol whereas reaction occurs at the I-position using the classical procedures.
- Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
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p. 13361 - 13372
(2007/10/03)
-
- The generation of iminium ions using chlorosilanes and their reactions with electron rich aromatic heterocycles
-
Dichlorodimethylsilane and trichloromethylsilane have been used to generate iminium ions from aminals and aminol ethers derived from secondary alkylamines, including glycine derivatives, in aprotic media which were shown to undergo reactions with electron rich aromatic heterocycles, including furan, to give mono-aminoalkylation products in good yields. Whereas chlorotrimethylsilane has been shown to generate iminium ions from aminol ethers, no evidence was adduced for the involvement of iminium ions using aminals. 2,5-Disubstitution of N-methylpyrrole was the major result in reactions of N-methylpyrrole with aminals in the presence of chlorotrimethylsilane where no build up of hydrogen chloride occurs and where chlorotrimethylsilane can function catalytically. Experimental results, including the use of bis(trimethylsilyl)acetamide as a proton scavenger, and some relative rate data, are presented that allow possible mechanisms to be evaluated.
- Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
-
p. 2941 - 2958
(2007/10/03)
-
- Development and Application of a Continuous Microwave Reactor for Organic Synthesis
-
A laboratory-scale continuous microwave reactor (CMR) has been developed and used to conduct organic syntheses routinely, rapidly, and safely in a range of solvents, under pressures up to 1400 kPa and at temperatures up to 200 deg C.Advantages and applications of the CMR are discussed, along with the rationale for the design.Reactions carried out with the CMR included nucleophilic substitution, addition, esterification, transesterification, acetalization, amidation, base- and acid-catalyzed hydrolysis, isomerization, decarboxylation, and elimination.Name reactions included the Michael addition, Hofmann degradation, Williamson ether synthesis, and the Mannich, Finkelstein, Baylis-Hillman, and Knoevenagel reactions.
- Cablewski, Teresa,Faux, Alan F.,Strauss, Christopher R.
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p. 3408 - 3412
(2007/10/02)
-
- Indole derivatives with antimycobacterial activity
-
1,3-Dinitro-2-(indol-3'-yl)-propanes 3 are synthesized by Michael reaction of nitromethane with the indolylnitroethenes 2. - Reaction of the aldehydes 4 and 10 with the benzylamines 12 as well as the reaction of the indolylalkylamines 6a and 9a with the benzaldehydes 11 lead to Schiff bases which are reduced to N-benzyl-(indol-3-ylmethyl)-amines 13 and N-benzyl-(indol-3-ylethyl)-amines 14, respectively; tert amines 16 are synthesized via the formamides 15, amines 18 are prepared according to Mannich. - Inhibitory effects on Mycobacterium tuberculosis H 37 Ra are investigated, a structure-activity relationship is discussed.
- Mahboobi,Grothus,Meindl
-
p. 105 - 114
(2007/10/02)
-
- A SYNTHESIS METHOD OF INDOLE-3-METHANAMINE AND/OR GRAMINE FROM INDOLE-3-CARBOXALDEHYDE, AND ITS APPLICATION FOR THE SYNTHESES OF BRASSININ, ITS 4-SUBSTITUTED ANALOGS, AND 1,3,4,5-TETRAHYDROPYRROLOQUINOLINE
-
Simple conversion method of indole-3-carboxaldehyde into gramine and/or indole-3-methanamine was developed.The present method realized short step syntheses of brassinin, 4-iodo-, methoxy-, 4-methoxy, and 4-nitrobrassinin, 4-methoxyindole-3-acetonitrile, and 1,3,4,5-tetrahydropyrroloquinoline.
- Yamada, Fumio,Kobayashi, Kensuke,Shimizu, Aya,Aoki, Naokatsu,Somei, Masanori
-
p. 2783 - 2804
(2007/10/02)
-
- A Facile Synthesis of 3-Substituted Indoles
-
1-Benzoyl-3-bromomethylindole (2a) or 1-benzenesulfonyl-3-bromomethylindole (2b) reacts with C, N, O, and P-containing nucleophiles to give potential intermediates for the synthesis of a wide range of indole alkaloids and pharmacologically important substances, in good to excellent yields.
- Nagarathnam, Dhanapalan
-
p. 953 - 958
(2007/10/02)
-
- MANNICH REACTIONS OF Π-EXCESSIVE HETEROCYLES USING BIS-(DIALKYLAMINO)METHANES AND ALKOXYDIALKYLAMINOMETHANES ACTIVATED WITH ACETYL CHLORIDE OR SULPHUR DIOXIDE
-
Π-Excessive heterocyles react rapidly with bis(dialkylamino)methanes (aminals) and alkoxydialkylaminomethanes (aminol ethers) in acetonitrile to afford Mannnich bases in good yields when ativated by means of an acidi reagent suh as acetyl chloride or sulphur dioxide: the principal ompound studied was N-methylpyrrole.
- Eyley, Stephen C.,Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
-
p. 2997 - 3000
(2007/10/02)
-
- Mannich Reactions of Nucleophilic Aromatic Compounds involving Aminals and α-Amino Ethers activated by Chlorosilane Derivatives; Catalysis by Chlorotrimethylsilane
-
Aminals and α-amino ethers afford N,N-dialkylmethyleneammonium salts by reaction with dichloro(dimethyl)- and trichloro(methyl)-silanes, but whereas chlorotrimethylsilane interacts with α-amino ethers to yield iminium salts, the reaction of the latter silane with aminals does not; in situ Mannich reactions may be carried out using these systems, and in the case of the reactions using chlorotrimethylsilane and aminals the reactions can be catalytic with respect to the silane.
- Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
-
p. 1161 - 1163
(2007/10/02)
-
- Radical Reactions of N-Heterocyclic Compounds. IV. ESR Investigation of H-Transfer between Aminic Antioxydants and Peroxy Radicals
-
The N-radicals of pyrazole-, imidazole- and indole-derivatives were prepared in comparatively high concentrations at room temperature in benzene or toluene and their e.s.r. signals were interpreted.In H-abstraction by free or to Co(III)-coordinated tert-butylperoxy radicals from bifunctional heterocyclic substituted amines 2-9, 11 the following efficiency was ascertained: unhindered - OH - > aniline-NH > heterocyclic-NH-, hindered OH-groups.No radical attack on the exocyclic NH2-group took place.The splitting constant concerning the heterocyclic nitrogen of nitroxyl radicals 5a, 10a was in the range aNendo = 0.7 to 0.85 mT in contrast to exocyclic nitroxyls 6a,8a,9a,11a possessing aNexo = 1.0 to 1.1 mT.The interruption of the ?-conjugation betweeen the heterocyclic and the aniline groups by insertion of a CH2-group led to the decrease of the stability of the generated N-radicals.In the case of anilinebenzimidazole 9 the Co(III)-complexed endocyclic aminyl radical 9b was observed simultaneously with the exocyclic nitroxyl radical 9a.
- Tkac, A.,Omelka, L.,Schulz, M.,Moegel, L.
-
-
- USE OF N,N-DIMETHYL(METHYLENE)AMMONIUM CHLORIDE IN THE FUNCTIONALIZATION OF INDOLES
-
The use of a preformed iminium salt has been found to provide superior yields in the generation of Mannich products from indoles.
- Kozikowski, Alan P.,Ishida, Hitoshi
-
-