- Synthesis and Antibacterial Activity of Novel 1H-indol-2-ol Derivatives
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A series of novel 1H-indol-2-ol derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight, tobacco bacterial wilt, and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and Ralstonia solanacearum. Especially, compound 4k demonstrated the best inhibitory effect against Xoo with half-maximal effective concentration (EC50) value of 8.27?μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper.
- Tu, Hong,Wu, Shou-Qun,Li, Xiao-Qin,Wan, Zhen-Chao,Wan, Jin-Lin,Tian, Kun,Ouyang, Gui-Ping
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Read Online
- Stereoselective synthesis of novel annulated thiopyrano indole derivatives from simple oxindole via intramolecular 1,3-dipolar cycloaddition reactions of nitrone and nitrile oxide
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Synthesis of some novel isoxazolidine/dihydroisoxazole annulated thiopyrano[2,3-b]indole derivatives from simple oxindole via 1,3-dipolar cycloaddition reaction involving nitrone and nitrile oxide as 1,3-dipole is reported.
- Majumder, Swarup,Bhuyan, Pulak J.
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Read Online
- Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source
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A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.
- Cheng, Didi,Li, Jingyi,Li, Yujin,Ling, Fei,Liu, Lei,Liu, Tao,Zhong, Weihui
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supporting information
p. 4107 - 4113
(2021/06/17)
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- A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes
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The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.
- Yang, Lei,Zhou, Shun,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng
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supporting information
p. 3678 - 3686
(2021/05/05)
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- ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020
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Paragraph 0158-0159; 0164-0165
(2020/05/01)
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- INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES- CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE
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The present invention relates to carbazoles of general formula (I), and process for the preparation thereof: wherein 'R1' is H, C1-C6 alkyl, benzyl, or allyl; R2 is H, C1-C6 alkyl, cyclopropyl, phenyl, aryl, heteroaryl, or NO2; R3 is H, C1-C6 alkyl, cyclopropyl, phenyl aryl, heteroaryl, 4-methoxy phenyl, 4-ethyl phenyl, 2-methyl phenyl, or 2-Fluoro phenyl; R4 is H, benzoyl, -CO2Et, -CHO, Br, or -OMe; R5 is OH, OMOM, OMe, CN, or OTf; R6 is H, or O-alkyl; and R3-R4 is -CHNCH2CH2-. This invention also relates to the process for the preparation of carbazomycin A of Formula (1), calothrixin B of Formula (2) and staurosporinone of Formula (3) involving carbazoles of general formula (I) as an intermediate.
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Page/Page column 31-32
(2020/10/20)
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- Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters
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The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.
- Yang, Lei,Zhao, Jian-Qiang,You, Yong,Wang, Zhen-Hua,Yuan, Wei-Cheng
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supporting information
p. 12363 - 12366
(2020/10/30)
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- Synthesis, Antiviral Activity, and Induction of Plant Resistance of Indole Analogues Bearing Dithioacetal Moiety
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A series of compounds with potential activity to induce plant resistance was synthesized from indole and thiol compounds and methodically evaluated for antiviral activity. The results indicated that some of the synthesized compounds had high antipotato virus Y (PVY), anticucumber mosaic virus, and antitobacco mosaic virus activities. Notably, compound D21 exhibited the best activity against PVY among these compounds in vivo, and the 50% effective concentrations (EC50) of protection activity is 122 μg/mL, which was distinctively better than the corresponding values for ribavirin (653 μg/mL), Ningnanmycin (464 μg/mL), and Xiangcaoliusuobingmi (279 μg/mL). Interestingly, we found that the protection activity of D21 was associated with improvement of chlorophyll content and defense-related enzyme activities. Moreover, D21 could trigger the malate dehydrogenase (MDH) signaling pathway, as further confirmed by the MDH activity evaluation. Hence, D21 can protect plants against viral activity and has potential as a novel activator for plant resistance induction.
- Wei, Chunle,Zhang, Jian,Shi, Jing,Gan, Xiuhai,Hu, Deyu,Song, Baoan
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p. 13882 - 13891
(2019/12/04)
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- Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes
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We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.
- Li, Feng,Zhou, Yirong,Yang, Heng,Wang, Ziqi,Yu, Qinqin,Zhang, Fang-Lin
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supporting information
p. 3692 - 3695
(2019/05/24)
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- Benzpyrole derivative containing dithioacetal unit, preparation method and application thereof
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The invention discloses a benzpyrole derivative containing a dithioacetal unit, a preparation method and application thereof. The benzpyrole derivative has the general structural formula (I) (being defined as in the specification), in the formula, R1 is substitution hydrogen or a halogen atom, R2 is a substitution aromatic ring, 1-propyl alcohol, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or dodecyl, and X is a halogen atom and the methyl. The benzpyrole derivative has the good biological activity for plant virus diseases, the preparation process is simple, and the production cost is low.
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Paragraph 0049; 0051; 0052
(2019/10/29)
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- Synthesis and Antimicrobial Activities of Novel Quinazolinone Acylhydrazone Derivatives Containing the Indole Moiety
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A series of novel quinazolinone acylhydrazone derivatives containing the indole moiety were designed, synthesized, and evaluated for their inhibition activities against some important phytopathogens in vitro. Antibacterial experiments indicated that some compounds exhibited remarkable inhibition activities against tested bacteria. Especially, the EC50 values of 7a (EC50?=?55.13?μg/mL against Xoo, EC50?=?56.92?μg/mL against Rs) demonstrated the best antibacterial activities against Xoo and Rs than the other compounds, and the control agents Bismerthiazol (EC50?=?89.80?μg/mL against Xoo) and Thiodiazole copper (EC50?=?189.52?μg/mL against Rs), moreover, compound 7o (EC50?=?50.80?μg/mL) displayed the excellent activity against Xac than the control Bismerthiazol (EC50?=?56.92?μg/mL).
- Li, Xiao-Qin,Gan, Yi-Yuan,Meng, Jiao,Li, Wen,Chen, Jie,Qi, Ya-Yun,Tian, Kun,Ouyang, Gui-Ping,Wang, Zhen-Chao
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p. 1382 - 1390
(2018/04/25)
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- Design, synthesis and anti-bacterial evaluation of novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety
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Novel 1,3,4-thiadiazole derivatives bearing a semicarbazone moiety were prepared and evaluated for their anti-bacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) by performing a turbidimetre test. The products were structurally characterised by IR, 1H NMR, 13C NMR, 19F NMR and HRMS. Anti-bacterial testing showed that most of the evaluated compounds (6a-6s) exhibited excellent activity (≥74.19%) against Xoo at a concentration of 200?μg/mL, with 50% effective concentration (EC50) values ranging from 12.21 to 67.20?μg/mL, which were superior to the commercial antibacterial agent bismerthiazol (92.23?μg/mL). Among them, compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((2-chlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6b) demonstrated good inhibitory activity against Xac (89.46% at 200?μg/mL) and Xoo (EC50 = 18.28?μg/mL); compound 2-((2-chloro-1H-indol-3-yl)methylene)-N-(5-((4-methoxybenzyl)thio)-1,3,4-thiadiazol-2-yl)hydrazine-1-carboxamide (6g) displayed excellent activity against Xoo with EC50 value of 12.21?μg/mL.
- Wan, Jinlin,Gan, Yiyuan,Hu, Weinan,Meng, Jiao,Tian, Kun,Li, Xiaoqin,Wu, Shouqun,Xu, Yang,Ouyang, Guiping,Wang, Zhenchao
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p. 443 - 450
(2018/03/12)
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- Method for simply and efficiently synthesizing caulerpin
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The invention belongs to the field of organic chemical synthesis and discloses a method for simply and efficiently synthesizing caulerpin. The method comprises the following steps: by taking 2-indolone as a raw material, firstly, performing halogenated acylation on the 2-indolone, protecting amino on indole, performing nucleophilic substitution at a site 2 of the amino, connecting malonic acid dimethyl, further performing decarboxylation and protection group removal so as to obtain 3-formyl-2-indole methyl acetate, and finally performing cyclization between two molecules, so as to obtain caulerpin. Compared with a disclosed method for synthesizing caulerpin, the method disclosed by the invention is simple in synthesis process, low in raw material cost, gentle in reaction condition, high inproduct purity, high in yield and easy in industrialization, and has a very high medical value and a wide market prospect.
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Paragraph 0043; 0044
(2018/07/30)
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- 2-hydroxyindole derivative as well as preparation method and use thereof
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The invention discloses a 2-hydroxyindole derivative as well as a preparation method and use thereof. The 2-hydroxyindole derivative has a structural formula (I) as follows: FORMULA, wherein R1 is 3-nitrophenyl, 2-methoxyphenyl, m-aminoacetophenone, p-aminoacetophenone, methylimino, ethylimino, isopropylimino, p-methylbenzimino, 4-trifluoromethylphenyl, benzylimino, 3-chloro-4-methylphenyl, 2, 4-dimethylphenyl, 2-ethylphenyl, 2, 6-dimethylphenyl, 4-methoxyphenyl, 2, 5-dimethoxyphenyl, 2, 5-dimethoxyphenyl, 3-chlorophenyl, m-methylphenyl, 4-hydroxyphenyl, 4-chloro-3-(trifluoromethyl) phenyl, 2, 5-dichlorophenyl and 2-ethoxyphenyl. The 2-hydroxyindole derivative provided by the invention is low in toxicity and environment-friendly, can improve the biological activity,, and can inhibit xanthomonas oryzae pv. oryzae, xanthomonas axonopodis pv. citri and ralstonia solanacearum.
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Paragraph 0040; 0044; 0045
(2017/09/29)
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- Copper-catalyzed Synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde by Step-wise and One-pot Three-component Huisgen's 1,3-dipolar Cycloaddition Reaction
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An efficient method for the synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde has been developed starting from oxindole and indole using Huisgen's 1,3-dipolar cycloaddition reaction of organic azides to alkynes. The effect of catalysts and solvent on these reactions has been investigated. Among all these conditions, while using CuSO4·5H2O, DMF was found to be the best system for this reaction. It could also be prepared in a one-pot three-component manner by treating equimolar quantities of halides, azides, and alkynes. The Huisgen's 1,3-dipolar cycloaddition reaction was performed using CuSO4·5H2O in DMF with easy work-up procedure.
- Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
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p. 3071 - 3076
(2017/10/03)
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- Tandem copper (Cu) catalysed N-arylation-vinylogous nitroaldol condensation of 3,5-disubstituted 4-nitropyrazoles
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A tandem process involving copper catalysed N-arylation and vinylogous nitroaldol condensation is described. The reaction of 3,5-dialkyl substituted 4-nitropyrazoles and ortho-halo substituted (hetero)aryl aldehydes or ketones furnished 3-nitropyrazolo[1,5-a]quinoline and heteroaryl-fused 3-nitropyrazolo[1,5-a]pyridine derivatives in moderate to high yields.
- Obulesu, Owk,Nanubolu, Jagadeesh Babu,Suresh, Surisetti
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supporting information
p. 8232 - 8240
(2015/08/03)
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- PROTEASOME ACTIVITY ENHANCING COMPOUNDS
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The present invention is directed to compounds having the Formula (I), (II), (III), (IV), and (V), compositions thereof, the methods of synthesis of the compouds of interest, and to methods for the treatment of a condition associated with a dysfunction in proteostasis, such as cancer, inflammatory conditions, neurodegeneration, metabolic conditions, comprising administering an effective amount of a compound of the invention.
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Page/Page column 127-128
(2015/06/03)
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- Synthesis of an azabicyclic framework towards (±)-actinophyllic acid
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Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo[4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product.
- Mortimer, Danny,Whiting, Matthew,Harrity, Joseph P.A.,Jones, Simon,Coldham, Iain
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p. 1255 - 1257
(2014/02/14)
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- Total synthesis of bouchardatine
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Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3- carbaldehyde (bouchardatine).
- Naik, Nilesh H.,Urmode, Tukaram D.,Sikder, Arun K.,Kusurkar, Radhika S.
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p. 1112 - 1114
(2013/09/24)
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- Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes
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Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/C-H functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling. Copyright
- Bhowmik, Subhendu,Pandey, Garima,Batra, Sanjay
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supporting information
p. 10487 - 10491
(2013/08/23)
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- Photoinduced chlorine atom-transfer cyclization/photohydrolysis of 3-acyl-2-chloro-N-(ω-phenylalkynyl)pyrroles: A one-pot synthesis of benzoyl-substituted fused pyrroles
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A one-pot synthesis of benzoyl-substituted fused pyrroles or indoles in moderate to high yields has been achieved by the photocyclization/ photohydrolysis reactions of N-(ω-phenylalkynyl)-2-chloropyrrole-3- carbaldehydes or 3-acyl-N-(ω-phenylbutynyl)-2-haloindoles in wet acetone. The formation of all these products could be inferred by a two-step reactions, namely, photoinduced chlorine atom-transfer cyclization and subsequent photohydrolysis.
- Lu, Shen-Ci,Wang, Wei-Xia,Gao, Pan-Liang,Zhang, Wei,Tu, Zhi-Feng
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supporting information; experimental part
p. 232 - 235
(2012/02/01)
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- Synthesis of some novel and complex thiopyrano indole derivatives from simple oxindole via intramolecular domino hetero Diels-Alder reactions
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Some novel polycyclic thiopyrano[2,3-b]indole derivatives 7 were synthesized from simple oxindole 1 by exploring intramolecular domino hetero Diels-Alder reactions strategy.
- Majumder, Swarup,Bhuyan, Pulak J.
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scheme or table
p. 137 - 140
(2012/01/17)
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- Rapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b] indole derivatives via one-pot three component reaction using organocatalysis
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A simple, green, and efficient one-pot three component strategy for the synthesis of 2-aryl-3-nitro-4-hydroxy-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives has been achieved by the combination of N-protected-2-chloro-3- formylindoles, sodium hydrosulfide with β-nitrostyrenes at room temperature in ethanol using DABCO as a catalyst. Furthermore, high enantio- and diastereoselectives' syntheses of title compounds have been achieved for the first time using cupreidine (5 mol %) as catalyst, providing good to excellent yields.
- Singh, Shivendra,Srivastava, Anvita,Samanta, Sampak
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supporting information
p. 6087 - 6090,4
(2020/08/20)
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- The tertiary amino effect: An efficient method for the synthesis of α-Carbolines
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Functionalized annelated α-Carbolines have been synthesized from oxindole following a tertiary amino effect reaction strategy. Georg Thieme Verlag Stuttgart New York.
- Majumder, Swarup,Bhuyan, Pulak J.
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experimental part
p. 173 - 176
(2011/03/22)
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- Photoinduced cyclization of 3-acyl-2-halo-1-[(ω-phenylethynyl)alkyl] indoles to azaheterocyclo[1,2,3- lm ]-fused benzo[ c ]carbazoles
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A one-pot synthesis of azaheterocyclo[1,2,3-lm]-fused benzo[c]carbazoles (2 and 3) has been developed by photocyclization of 3-acyl-2-halo-1-[(ω- phenylethynyl)alkyl] indoles (1) in good to excellent yields. All products are formed from 1 via two sequential photocyclization reactions. Two products, 9-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2-h) and 7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3-h), are produced in the photocyclization of 2-halo-1-[(ω-phenylethynyl)alkyl]indole-3- carbaldehydes (1-h). In contrast, only products 2-h are produced in the photocyclization of 3-acetyl-2-chloro-1-[(ω-phenylethynyl)alkyl]indole-3- carbaldehydes (1o - t). The 9-H in 3-h (n = 2) does originate from the formyl group in 1-h via 1,5-hydrogen shift. The structures of three new products, 9-bromo-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2b), 9-chloro-10-methyl-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (3h) and 12-chloro-7,8-dihydro-6H-benzo[c]pyrido[1,2,3-lm]carbazole (2w), have been corroborated by single-crystal X-ray structural analyses.
- Lu, Shenci,Wang, Ren,Yang, Yi,Li, Yang,Shi, Zongjun,Zhang, Wei,Tu, Zhifeng
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experimental part
p. 5661 - 5669
(2011/09/16)
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- One-pot synthesis of fused benzo[c]carbazoles by photochemical intramolecular annulation of 3-acyl-2-haloindoles with tethered styrenes
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An efficient procedure for the synthesis of fused benzo[c]carbazoles has been achieved in moderate to high yields by the one-pot photochemical annulation of 3-acyl-2-haloindoles with tethered styrenes by photoinduced electron-transfer coupling, electrocyclic reactions, and deacylative aromatization in the presence of pyridine. Fused furo[2,3-c]carbazoles were also synthesized under the same conditions. 5,6-Dihydrobenzo[c]pyrrolo[1,2,3-lm] carbazoles were oxidized by DDQ to afford aromatic benzo[c]pyrrolo[1,2,3-lm] carbazole products in moderate to high yields.
- Lu, Shen-Ci,Wei, Shi-Chao,Wang, Wei-Xia,Zhang, Wei,Tu, Zhi-Feng
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supporting information; experimental part
p. 5905 - 5910
(2011/11/06)
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- An efficient one-pot, three-component reaction: Synthesis of complex-annelated α-carbolines via an intramolecular [3+2]-dipolar cycloaddition reaction
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Novel annelated α-carbolines have been synthesized from oxindole using three components in a one-pot procedure involving an intramolecular [3+2]-dipolar cycloaddition reaction of azides to nitriles. Georg Thieme Verlag Stuttgart ? New York.
- Majumder, Swarup,Bhuyan, Pulak J.
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scheme or table
p. 1547 - 1550
(2011/08/04)
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- Photoinduced intramolecular addition of 3-acyl-2-haloindoles to alkenes
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1,2-Fused indoles and pyrroles were prepared via an efficient intmolecular photoaddition reaction of 1-(ωalkenyl)-2 haloindole-3-carbaldehydes and 1-(ωalkenyl)-2 chloropyrrole-3-carbaldehydes. The presence of an acyl group was necessary for the photocycizntion reactions. The halogen-atom retained exo and endo cyclization prodects were generally prodeced with result similar to those of atom transfer cyclization reaction. in contrast, unsaturated cyclization prodects were obtained in the photoreactions of substrates having monthyl groups on vinyl group.
- Lu, Shen-Ci,Duan, Xiao-Yong,Shi, Zong-Jun,Li, Bing,Ren, Yu-Wei,Zhang, Wei,Zhang, Yong-Hui,Tu, Zhi-Feng
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supporting information; experimental part
p. 3902 - 3905
(2009/12/03)
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- Intramolecular photochemical cross-coupling reactions of 3-acyl-2-haloindoles and 2-chloropyrrole-3-carbaldehydes with substituted benzenes
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Highly efficient syntheses of indolo[2,1-a]isoquinolines, indolo[2,1-a][2]benzazepines, pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]benzazepines in excellent yields have been achieved by the intramolecular photochemical cross-coupling reactions of 3-acyl-2-halo-N- (ω-arylalkyl)indoles and 2-chloro-N-(ω-arylalkyl)pyrrole-3- carbaldehydes in acetone. A new heterocyclic ring system - pyrrolo[1,2-d][1,4] benzoxazepine - has also been constructed for the first time in this work by the photocyclization of 2-chloro-N-(2-phenoxyethyl)pyrrole-3-carbaldehyde.
- Lu, Shen-Ci,Zhang, Xi-Xia,Shi, Zong-Jun,Ren, Yu-Wei,Li, Bing,Zhang, Wei
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supporting information; experimental part
p. 2839 - 2844
(2010/03/24)
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- Creation of new promoters for plant's root growth: its application for the syntheses of vulcanine and borreline, and for combating desertification at gobi desert in inner mongolia 1#
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Abstract - Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant.
- Somei, Masanori,Sayama, Shinsuke,Naka, Katsumi,Shinmoto, Kotaro,Yamada, Fumio
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experimental part
p. 537 - 554
(2009/09/25)
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- Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.
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The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta-ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity. Reaction: see text.
- Deng,Konopelski
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p. 3001 - 3004
(2007/10/03)
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- Synthesis of 2-amino-4H-thiazolo[5,4-b]indole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity
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In DMSO-solution 2-amino-4H-thiazolo[5,4-b]indole is converted into a complex mixture of colored products. The three major conversion end-products, of which two are inhibitors of protein tyrosine phosphatases (PTPs), were isolated by chromatographic methods and their structures characterized by spectroscopic analysis, including NMR and MS combined with computer assisted structure elucidation, and, finally, confirmed by independent chemical synthesis. Synthesis of 2-amino-4H-thiazolo[5,4-b]indole as well as its N-acetyl derivatives prepared from either oxindole or 2-bromo-1-(2-nitro-phenyl)ethanone is described.
- Breinholt,Jeppesen,Branner,Olsen,Moller,Nielsen,Andersen
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p. 569 - 577
(2007/10/03)
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- ANTAGONISTS, THEIR PREPARATION AND USE
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The present invention relates to therapeutically active non competitive antagonists, acting selectively at the metabotropic glutamate receptor. The novel compounds are useful in treating diseases in the central nervous system by modulating synaptic transmission via the metabotropic glutamate receptor.
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- Tyrosine kinase inhibitors. 6. Structure-activity relationships among N- and 3-substituted 2,2'-diselenobis(1H-indoles) for inhibition of protein tyrosine kinases and comparative in vitro and in vivo studies against selected sulfur congeners
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A small series of 2,2'-diselenobis(1H-indoles) was synthesized as redox- modified congeners of our earlier reported 2,2'-dithiobis(1H-indole) series. Utilizing chemistry similar to that developed earlier for the disulfur series, compounds were made from 2-halogeno-3-indolecarboxylic acid precursors bearing various polar functionality at the C-3 position and small alkyl substituents at the N-1 position of the indole nucleus. Additional compounds were derived from (R)- or (S)-tryptophan via a novel application of diselenium dichloride as an electrophilic source of diselenium, and a much improved process to a 2,2'-dithiobis(1H-indole) congener was developed utilizing disulfur dichloride as a source of disulfur. Against isolated epidermal growth factor receptor (EGFr), platelet-derived growth factor receptor (PDGFr), and v-src tyrosine kinases, compounds in this series displayed broad inhibitory activity with IC50 = 0.9 to > 100 μM vs EGFr, 3.4 to >50 μM vs PDGFr, and 0.4-6.7 μM vsv-src. In general, compounds derived from tryptophan displayed the greatest potency against EGFr and those from 2-halogeno-3-indolecarboxylic acids greater potency against PDGFr and v- src. Enzyme kinetics studies showed that both classes of compounds display primarily noncompetitive inhibition with respect to either ATP or peptide substrate. The sulfhydryl reducing agent dithiothreitol (DTT) caused a general decrease in inhibition of the EGFr and v-src tyrosine kinases by both the diselenium and disulfur series with the reversal of enzyme inhibition occurring less readily within the diselenium series. In whole cell studies, compounds of this class were growth inhibitory against Swiss 3T3 mouse fibroblasts with IC50 values from 0.5 to 19.5 μM, and the observed SAR was different from that of the 2,2'-dithiobis(1H-indoles). A comparative study in the same cell line on the effects of the 2,2'-diselenobis(lH-indole) derived from (R)-tryptophan vs its disulfur congener on growth factor mediated tyrosine phosphorylation showed that this compound significantly inhibited EGFr and PDGFr (in response to its ligand) autophosphorylation with complete suppression at 25 and 5 μM, respectively. Tyrosine phosphorylation of an 85 kDa protein typically phosphorylated in response to bFGF was also exquisitely sensitive to this compound, and it displayed inhibitory effects on DNA, RNA, and protein synthesis at submicromolar concentrations. The disulfur congener exhibited a qualitatively similar pattern; however, its potency was 10-fold less. This same diselenium/disulfur pair was evaluated in vivo against the B16 melanoma, colon carcinoma 26, and M5076 sarcoma murine tumors, and the A431 epidermoid, and C6 glioma human tumor xenografts. At maximum tolerated doses (1.8 and 5.0 mg/kg/injection, respectively), neither the diselenium nor disulfur congener was effective against the C6 glioma when administered intraperitoneally on a d 1-9 schedule. Studies were also carried out against the A431 epidermoid xenograft to evaluate the same pair of compounds via continuous subcutaneous infusion from Alzet miniosmotic pumps. The maximum dose that could be administered daily was limited by compound solubility. Neither compound produced an antitumor effect in a 7-day continuous infusion study. In the 27-day study, the disulfur compound was inactive whereas the diselenium compound produced a 10.8-day growth delay without appreciable treatment related weight loss. The in vitro and in vivo findings offer a mechanistic rationale as to why the 2,2'-diselenobis(1H-indoles) are more potent inhibitors than their disulfur congeners.
- Showalter, H. D. Hollis,Sercel, Anthony D.,Leja, Boguslawa M.,Wolfangel, Craig D.,Ambroso, Linda A.,Elliott, William L.,Fry, David W.,Kraker, Alan J.,Howard, Curtis T.,Lu, Gina H.,Moore, Charles W.,Nelson, James M.,Roberts, Bill J.,Vincent, Patrick W.,Denny, William A.,Thompson, Andrew M.
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p. 413 - 426
(2007/10/03)
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- THIENO[2,3-B-INDOLE DERIVATIVES AND THEIR USE FOR TREATING CENTRAL NERVOUS SYSTEM DISEASES RELATED TO THE METABOTROPIC GLUTAMATE RECEPTOR SYSTEM
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The present invention relates to therapeutically active heterocyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful in treating diseases in the central nervous system related to the metabotropic glutamate receptor system.
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- PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES
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An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.
- Kawasaki, Toshiya,Kodama, Atsushi,Nishida, Tokiko,Shimizu, Kazuhisa,Somei, Masanori
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p. 221 - 227
(2007/10/02)
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