共查询到20条相似文献,搜索用时 15 毫秒
1.
Subramanian Vedhanarayanan Karthikeyan Subbu Perumal Krithika Arun Shetty Perumal Yogeeswari Dharmarajan Sriram 《Bioorganic & medicinal chemistry letters》2009,19(11):3006-3009
A series of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles has been synthesised regioselectively in good yields from the reaction of 5-aryldihydro-3(2H)-thiophenones and arylhydrazine hydrochloride. This reaction is found to be assisted by microwaves. The thieno[3,2-b]indoles were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among 22 compounds screened, [2-(2,4-dichlorophenyl)-7-fluoro-3,4-dihydro-2H-thieno[3,2-b]indole] (6t) was found to the most active compound with MIC of 0.4 μg/mL against MTB and MDR-TB. 相似文献
2.
Narayana B Ashalatha BV Vijaya Raj KK Fernandes J Sarojini BK 《Bioorganic & medicinal chemistry》2005,13(15):4638-4644
An efficient and modified synthesis of ethyl-4-nitro/5-nitro/6-nitro and 7-nitroindole-2-carboxylates is described. Carbohydrazides of corresponding ethyl nitroindole-2-carboxylates underwent smooth one-step transformation to 1,3,4-oxadiazolyl nitroindoles (4a-l) on reaction with aromatic carboxylic acids in the presence of phosphorus oxychloride. An alternate method to synthesize 1,3,4-oxadiazolyl nitroindoles is also described. Among the newly synthesized 1,3,4-oxadiazolyl nitroindoles, a few compounds are studied for anti-inflammatory activity. 相似文献
3.
A.Ian Scott 《Bioorganic chemistry》1974,3(4):398-429
A review of the rationale and methodology for the laboratory construction of the major classes of indole alkaloid based on their known or presumed biosynthesis is presented. The experimental results obtained provide analogies for the principal condensation and rearrangement reactions uncovered in biochemical investigations in this field and suggest new incorporation experiments. The prediction and discovery of new classes of alkaloid based on the observed transformations have been made and, in turn, new theories have been developed to explain some of the hitherto unsolved problems of biotransformation and structure in this series.Finally, the suggestion is made that many of the complex structures encountered in the various families may arise through rather unspecific processes, some indeed of a nonenzymic nature. 相似文献
4.
Nettekoven M 《Bioorganic & medicinal chemistry letters》2001,11(16):2169-2171
The synthesis of two indole derivative libraries is described. 2-Acyl-3-amino-indoles 4 can easily be accessed by treatment of the intermediates 3 with bases in a one-pot reaction sequence whereas the reaction of the isolated intermediates 5 (R(3)=aromatic-, heteroaromatic, or cycloalkyl) with acid chlorides yielded the novel indole derivatives 6. The products were purified by reversed phase column chromatography and obtained in multi-milligram quantities in acceptable yields. 相似文献
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Sugino K Yoshimura H Nishikawa T Isobe M 《Bioscience, biotechnology, and biochemistry》2008,72(8):2092-2102
Regioselectivity of Larock indole synthesis, a palladium-catalyzed heteroannulation between o-iodoaniline and internal acetylene, was estimated using acetylenes substituted with ester and/or Boc-protected amine at the homopropargylic position and with perbenzyl- and unprotected glucose. Low to moderate regioselectivities were observed in all the cases, indicating these functional groups do not exert good directing effects, in the Larock indole synthesis. 相似文献
7.
Madan G. Barthakur 《Steroids》2009,74(9):730-904
The preparation of ring-A fused pyrimidines at the steroidal 2,3-position is herein described. The novel steroidal pyrimidines were prepared from the solid phase three-component reaction of 2-hydroxymethylene-3-keto steroids, arylaldehydes and ammonium acetate under microwave irradiation. 相似文献
8.
Magedov IV Luchetti G Evdokimov NM Manpadi M Steelant WF Van Slambrouck S Tongwa P Antipin MY Kornienko A 《Bioorganic & medicinal chemistry letters》2008,18(4):1392-1396
Diversely substituted 2-pyrrolines have been prepared by a novel multicomponent process involving a reaction of various N-(aryl- and alkylsulfonamido)-acetophenones with aldehydes and malononitrile. While the reaction is highly regioselective, it is not stereoselective, generating a mixture of cis and trans 2-pyrrolines. A number of analogs from both cis and trans 2-pyrroline libraries were found to have antiproliferative activity in human cancer cell lines. 相似文献
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Induction of indole synthesis in young appendix sections ofSauromatum guttatum Schott was studied. The inducer, known ascalorigen, a compound synthesized in the mature staminate flowerbuds, is capable of triggering a rapid metabolic spurt in theappendix of the inflorescence. The induced indole-formationlasts for only a short period of time, and is similar to thenormal pattern of indole synthesis. Under the experimental conditions,indole was detectable after 7 to 8 hr of calorigen treatmentbut had disappeared about 35 hr later. The moment when indoleis present in maximal amount coincides with that of maximalheat production, i.e., about 27 hr after the application ofcalorigen. A simple and sensitive bioassay for detection ofcalorigen, based on the formation of indole, could be devised. Calorigen also causes, to a lesser extent, a temperature-riseof those young floral parts (male, female and sterile tissues)where indole is not detectable at any time. The time sequenceof the induced production of heat for the various floral partsmimics that of a natural metabolic flare-up. Extracts prepared from the mature staminate flowers of Arummaculatum L., Arum dioscoridis Sibth and Sm., and Dracunculusvulgaris Schott were all able to induce the formation of indolein the appendix of Sauromatum in a fashion similar to that causedby the staminate flower extract of this plant. (Received February 12, 1972; ) 相似文献
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A novel one-pot three-component condensation reaction of an aldehyde, β-ketoester and 2-aminobenzimidazole or 2-aminobenzothiazole in 1,1,3,3-N,N,N′,N′-tetramethylguanidinium trifluoroacetate as an ionic liquid is described. During the course of this reaction 4H-pyrimido[2,1-b]benzimidazoles or 4H-pyrimido[2,1-b]benzothiazoles are formed in high yields at 100 °C. The ionic liquid can be recovered conveniently and reused efficiently. 相似文献
13.
The Sonogashira alkynylation of acid chlorides can be efficiently conducted in less than an hour by performing the reaction in tetrahydrofuran as a solvent and in the presence of one stoichiometrically necessary equivalent of triethylamine as a base. This approach also opens new avenues for consecutive one-pot multicomponent reactions. As an example, the one-pot three-component pyrimidine synthesis illustrates the versatility of this modified Sonogashira protocol as an entry to diversity-oriented heterocycle synthesis in a one-pot fashion. The protocol can be completed within a few hours. 相似文献
14.
《Bioorganic & medicinal chemistry》2014,22(1):366-373
Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line. 相似文献
15.
Chunlan Pu Rong-Hua Luo Mengqi Zhang Xueyan Hou Guoyi Yan Jiang Luo Yong-Tang Zheng Rui Li 《Bioorganic & medicinal chemistry letters》2017,27(17):4150-4155
The crystal structure of viral infectivity factor (Vif) was reported recently, which makes it possible to design new inhibitors against Vif by structure-based drug design. Through analysis of the protein surface of Vif, the C2 pocket located in the N-terminal was found, which is suit for developing small molecular inhibitors. Then, in our article, fragment-based virtual screening (FBVS) was conducted and a series of fragments was obtained, among which, Zif-1 bearing indole scaffold and pyridine ring can form H-bonds with Tyr148 and Ile155. Subsequently, 19 derivatives of Zif-1 were synthesized. Through the immune-fluorescence staining and Western blot assays, Zif-15 shows potent activity in inhibiting Vif-mediated A3G degradation. Further docking experiment shows that Zif-15 form H-bond interactions with residues His139, Tyr148 and Ile155. Therefore, Zif-15 is a promising lead compound against Vif that can be used to treat AIDS. 相似文献
16.
Chen JJ Wei Y Williams JD Drach JC Townsend LB 《Nucleosides, nucleotides & nucleic acids》2005,24(10-12):1417-1437
2,5, 6-Trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB), 2-bromo-5, 6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BDCRB) and 2-benzylthio-5,6-dichloro-1-(beta-D-ribofuranosyl)benzimidazole (BTDCRB) are benzimidazole nucleosides that exhibit strong and selective anti-HCMV activity. Polyhalogenated indole C-nucleosides were prepared as 1-deaza analogs of the benzimidazole nucleosides TCRB and BDCRB. A mild Knoevenagel coupling reaction between an indol-2-thione and a ribofuranose derivative was developed for the synthesis of 2-benzylthio-5, 6-dichloro-3-(beta-D-ribofuranosyl)indole (12). 3-(beta-D-ribofuranosyl)-2,5,6-trichloroindole (16) was prepared from 12 in 4 steps. A Lewis acid-mediated glycosylation method was then developed to prepare the targeted 2-haloindole C-nucleoside 16 stereoselectively in four steps from the corresponding 2-haloindole aglycons. Only 12 was active against HCMV but it also was somewhat cytotoxic. 相似文献
17.
David J Rawson Kevin N Dack Roger P Dickinson Kim James 《Bioorganic & medicinal chemistry letters》2002,12(2):125-128
Conformational constraint has been used as the key design element in the identification of a series of potent and selective ET(A) antagonists. The most potent antagonist, 32, (ET(A) IC(50)=0.55nM) is 722-fold selective over the ET(B) receptor, as measured by binding experiments. 相似文献
18.
Summary A gas-sensor-dip-electrode (GSDE) for continuous on-line measurement of indole in liquid was developed. The response time of the GSDE with a gas-sensor from SnO2-type could be reduced to 20 seconds with a Cuprophan membrane (thickness, 37m). A linear range for the indole determination from 0 to 2 g l–1 is possible and the sensor readings agreed well with simultaneous indole determination by HPLC. 相似文献
19.
R Hossein Nia M Mamaghani K Tabatabaeian F Shirini M Rassa 《Bioorganic & medicinal chemistry letters》2012,22(18):5956-5960
Novel fused 1H-benzo[f]chromen-indole derivatives were synthesized regioselectivly in good to high yields by triethyl amine catalyzed condensation of 3-cyanoacetylindoles, β-naphthol and aryl aldehydes in methanol under ultrasounic irradiations and conventional conditions. The easy work-up of the products, rapidity, and mild reaction conditions are notable features of this protocol. The antibacterial activity of the selected products was examined. Some products showed promising activities. 相似文献
20.
Indole containing compounds have acquired conspicuous significance due to their wide spectrum of biological activities. Synthesis of a series of enantiomerically pure indole derivatives 3a-r via Friedel–Crafts alkylation of indole 1 with enones 2a-r were described here. The products were isolated in a moderate to excellent yields (upto 89%) with excellent enantioselectivities (upto 99.9% ee). These compounds 3a-r were evaluated for their in vitro α-glucosidase inhibitory activity and some of them were identified as potent inhibitors (IC50 = 4.3 ± 0.13–43.9 ± 0.51 μM) with several fold higher activity than the clinically used α-glucosidase inhibitor, acarbose (IC50 = 840 ± 1.73 μM). To the best of knowledge, this is the first report of the propanone substituted indole ring containing compounds by in vitro α-glucosidase enzyme inhibition. 相似文献