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1.
Larry D. Bratton Bruce D. Roth Bharat K. Trivedi Paul C. Unangst 《Journal of heterocyclic chemistry》2000,37(5):1103-1108
The preparation of several novel 3,5‐substituted‐indole‐2‐carboxamides is described. A 5‐nitro‐indole‐2‐carboxylate was elaborated to the 3‐benzhydryl ester, N‐substituted ester, and carboxylic acid intermedi ates, followed by conversion to the amide and then reduction of the 5‐nitro group to the amine. Indole‐2‐carboxamides with 3‐benzyl and 3‐phenyl substituents were prepared in four steps from either a 3‐bromo indole ester using the Suzuki reaction or from a 3‐keto substituted indole ester. N‐Alkylation of ethyl indole‐2‐carboxylate, followed by amidation and catalytic addition of 9‐hydroxyxanthene gave a 3‐xanthyl‐indole‐2‐carboxamide analog and a spiropyrrolo indole as a side product. 相似文献
2.
N‐Ethylation of substituted ethyl 1H‐indole‐2‐carboxylates with iodoethane and potassium carbonate gave substituted ethyl 1‐ethyl‐1H‐indole‐2‐carboxylates. The later compounds on treatment with a range of aryl amines with varying structural complexity, gave the desired ethyl 1H‐indole‐2‐carboxamide analogues. 相似文献
3.
Regio‐ and Chemoselective N‐1 Acylation of Indoles: Pd‐Catalyzed Domino Cyclization to Afford 1,2‐Fused Tricyclic Indole Scaffolds 下载免费PDF全文
Yongxian Liu Yuanqiong Huang Hongjian Song Yuxiu Liu Prof. Qingmin Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(14):5337-5340
A concise method for the synthesis of 1,2‐fused tricyclic indole scaffolds by domino cyclization involving a Pd‐catalyzed Sonogashira coupling, indole cyclization, regio‐ and chemoselective N‐1 acylation, and 1,4‐Michael addition is reported. This method provides straightforward access to tetrahydro[1,4]diazepino[1,2‐a]indole and hexahydro[1,5]diazocino[1,2‐a]indole scaffolds. 相似文献
4.
Prenylated Indole Alkaloid Derivatives from Marine Sediment‐Derived Fungus Penicillium paneum SD‐44 下载免费PDF全文
Three new prenylated indole alkaloids, including two β‐carbolines, penipalines A and B ( 1 and 2 , resp.), and one indole carbaldehyde derivative, penipaline C ( 3 ), as well as two known indole derived analogs, 4 and 5 , were isolated from the deep‐sea‐sediment derived fungus Penicillium paneum SD‐44 cultured in a 500‐l bioreactor. The structures of the new compounds were determined on the basis of 1D‐ and 2D‐NMR spectroscopy, as well as by high‐resolution mass spectrometry. The new compounds 2 and 3 showed potent cytotoxic activities against A‐549 and HCT‐116 cell lines. 相似文献
5.
《Journal of carbohydrate chemistry》2013,32(7-8):743-751
Indolyl N‐glycoside analogs were obtained by a two‐step sequence via indole N‐thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N‐thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N‐ over C3‐acylation. Treatment of the ω‐hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N‐(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the ω‐hydroxyl group can give access to tetrahydrothiophene N‐glycosides. 相似文献
6.
An efficient, stereocontrolled total synthesis of the complex indole‐diterpene alkaloid (?)‐21‐isopentenylpaxilline ( 1 ) has been achieved. Key elements of the synthesis include the stereocontrolled construction of the advanced eastern hemisphere (?)‐ 68 , involving a highly efficient union of the eastern and western fragments (?)‐ 68 and 5 exploiting our 2‐substituted indole synthesis, application of the Negishi π cycloalkylation tactic as a new, potentially general protocol for the construction of ring C, and the fragmentation of a β,γ‐epoxy ketone to introduce the tertiary OH group at C(13) in the indole diterpene skeleton. 相似文献
7.
C. Montagne N. Laurent B. Joseph J.‐Y. Mrour 《Journal of heterocyclic chemistry》2005,42(7):1433-1441
Preparation of the 5‐substituted azepino[3,4‐b]indole core structure can be realised through a catalytic Heck reaction. The scope and limitations of this methodology are reported. The reactivity of di‐tert‐butyl 5‐ethoxycarbonylmethylene‐1,3,4,5‐tetrahydro‐1‐oxoazepino[3,4‐b]indole‐2,10‐dicarboxylate (1) was investigated in order to prepare the indole analogue of hymenialdisine and derivatives. 相似文献
8.
Indoles are ubiquitous structures that are found in natural products and biologically active molecules. The synthesis of indoles and indole‐involved synthetic methodologies in organic chemistry have been receiving considerable attention. Indole‐N‐carboxylic acids and derived indole‐N‐carboxamides are intriguing compounds, which have been widely used in organic synthesis, especially in multicomponent reactions and C?H functionalization of indoles. This Minireview summarizes the advances of reactions involving indole‐N‐carboxylic acids and indole‐N‐carboxamides in organic chemistry, and discusses the synthetic potential and perspective of this field. 相似文献
9.
Qing Zhang Liangbiao Fan Qiaomei Lu Xiaozhang Yu Meina Liang Jinfang Nie Ningjie Li Lan Zhang 《Journal of separation science》2019,42(16):2687-2695
As signal molecules, auxins play an important role in mediating plant growth. Due to serious interfering substances in plants, it is difficult to accurately detect auxins with traditional solid‐phase extraction methods. To improve the selectivity of sample pretreatment, a novel molecularly imprinted polymer ‐coated solid‐phase microextraction fiber, which could be coupled directly to high‐performance liquid chromatography, was prepared with indole acetic acid as template molecule for the selective extraction of auxins. The factors influencing the polymer formation, such as polymerization solvent, cross‐linker, and polymerization time, were investigated in detail to enhance the performance of indole acetic acid‐molecularly imprinted polymer coating. The morphological and chemical stability of this molecularly imprinted polymer‐coated fiber was characterized by scanning electron microscopy, infrared spectrometry, and thermal analysis. The extraction capacity of the molecularly imprinted polymer‐coated solid‐phase microextraction fiber was evaluated for the selective extraction of indole acetic acid and indole‐3‐pyruvic acid followed by high‐performance liquid chromatography analysis. The linear range for indole acetic acid and indole‐3‐pyruvic acid was 1–100 µg/L and their detection limit was 0.5 µg/L. The method was applied to the simultaneous determination of two auxins in two kinds of tobacco (Nicotiana tabacum L and Nicotiana rustica L) samples, with recoveries range from 82.1 to 120.6%. 相似文献
10.
Bernhard Irlinger Andrea Bartsch Hans‐Joachim Krmer Peter Mayser Wolfgang Steglich 《Helvetica chimica acta》2005,88(6):1472-1485
Eleven new indole alkaloids were isolated from cultures of the human pathogenic yeast Malassezia furfur after addition of L ‐tryptophan as the sole N‐source: pityriacitrin B ( 2 ), the malassezindoles A ( 3 ) and B ( 4 ), malassezialactic acid ( 6 ), the malasseziazoles A ( 7 ), B ( 8 ), and C ( 9 ), pityriazole ( 10 ), malasseziacitrin ( 11 ), and malassezione ( 12 ), along with the known d‐ indole‐3‐lactic acid (=(αR)‐α‐hydroxy‐1H‐indole‐3‐propanoic acid 5 ), and 2‐hydroxy‐1‐(1H‐indol‐3‐yl)ethanone ( 13 ). The structural elucidation of these compounds was performed by spectroscopic methods (MS as well as 1D‐ and 2D‐NMR). The biogenetic relationships (Scheme) and biological activities of the new metabolites are discussed. 相似文献
11.
Du‐Qiang Luo Yu‐Peng Chen Jun Zhang Bao‐Zhong Shi Zi‐Qi Yang Chuan Chen 《Helvetica chimica acta》2013,96(2):309-312
A new glycine derivative, podocarpiamide ( 1 ), a new indole alkaloid, 1‐methoxy‐1H‐indol‐3‐ethanol ( 2 ), together with two known compounds, 1‐methoxy‐1H‐indole‐3‐acetic acid ( 3 ) and methyl 1‐methoxy‐1H‐indole‐3‐acetate ( 4 ), were isolated from the fermentation broth of the plant endophytic fungus Pestalotiopsis podocarpi. Their structures were elucidated by extensive spectroscopic analysis including 1D‐ and 2D‐NMR (HSQC, HMBC, and COSY) and MS experiments. Compound 1 has an interesting unusual carbamic acid structure. 相似文献
12.
Carlos Camacho‐Camacho Irma Rojas‐Oviedo M. Angeles Paz‐Sandoval Jorge Cárdenas Alfredo Toscano Marcel Gielen Lidia Barrón Sosa Francisco Sánchez Bártez Isabel Gracia‐Mora 《应用有机金属化学》2008,22(3):171-176
The synthesis, characterization and cytotoxic properties in vitro of tri‐n‐butyltin 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 1 ), tri‐phenyltin 1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 2 ), tetra‐n‐butyltin[bis‐1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetato]distannoxane ( 3 ) and di‐n‐butyltin bis‐1‐(4‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1H‐indole‐3‐acetate ( 4 ) are described. These compounds have been characterized by 1H, 13C and 119Sn NMR spectroscopy in solution and 119Sn NMR in the solid state, infrared spectroscopy, elemental analysis and X‐ray diffraction for compound 1 . The growth inhibition effects of compounds 1–4 against the lung adenocarcinoma cell line SK‐LU‐1 as well as the cervical cancer cell line HeLa were determined. Compounds 1 and 2 exhibit cytotoxic activity, whereas compounds 3 and 4 are inactive. Copyright © 2008 John Wiley & Sons, Ltd. 相似文献
13.
Jens Breinholt Claus Bekker Jeppesen Sven Branner Carl Erik Olsen Niels Peter Hundahl Mller Bjarne Hilmer Nielsen Henrik Sune Andersen 《Journal of heterocyclic chemistry》2001,38(3):569-577
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 phos‐phatases (PTPs), were isolated by chromatographic methods and their structures characterized by spectro‐scopic 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. 相似文献
14.
A facile one‐pot, three‐component protocol for the synthesis of novel spiro[3H‐indole‐3,2′‐thiazolidine]‐2,4′(1H)‐diones by condensing 1H‐indole‐2,3‐diones, 4H‐1,2,4‐triazol‐4‐amine and 2‐sulfanylpropanoic acid in [bmim]PF6 (1‐butyl‐3‐methyl‐1H‐imidazolium hexafluorophosphate) as a recyclable ionic‐liquid solvent gave good to excellent yields in the absence of any catalyst (Scheme 1 and Table 2). The advantages of this protocol over conventional methods are the mild reaction conditions, the high product yields, a shorter reaction time, as well as the eco‐friendly conditions. 相似文献
15.
Wolfram Wilk Dipl.‐Chem. Andrea Nören‐Müller Dr. Markus Kaiser Dr. Herbert Waldmann Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(44):11976-11984
Macrolines constitute a class of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology‐oriented synthesis (BIOS). We have presented a solid‐phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet–Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various additional diversification procedures, such as Pd‐catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10‐substituted cycloocta[b]indole derivatives. Finally, solution‐phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid‐phase synthesis. 相似文献
16.
Riccardo Egris Mercedes Villacampa Prof. J. Carlos Menéndez Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(41):10930-10939
The reaction of vinyl Grignard reagents with o‐methoxynitroarenes containing an electron‐releasing substituent para to the nitro group proceeds through a pathway that is different from the initially expected Bartoli indole synthesis. Thus, instead of giving fused indole derivatives, these reactions provide a very mild and efficient new procedure for the synthesis of synthetically relevant aromatic systems containing an o‐nitrovinyl moiety, such as 5‐nitro‐4‐vinylindoles, 6‐nitro‐7‐vinylindoles, 6‐nitro‐5‐vinyl‐2(1H)quinolinones, and 4‐nitro‐3‐vinylanilines. 相似文献
17.
Application of a Palladium‐Catalyzed C−H Functionalization/Indolization Method to Syntheses of cis‐Trikentrin A and Herbindole B 下载免费PDF全文
Raul A. Leal Caroline Bischof Youjin V. Lee Shota Sawano Christopher C. McAtee Luke N. Latimer Zachary N. Russ Prof. John E. Dueber Prof. Jin‐Quan Yu Prof. Richmond Sarpong 《Angewandte Chemie (International ed. in English)》2016,55(39):11824-11828
We describe herein formal syntheses of the indole alkaloids cis‐trikentrin A and herbindole B from a common meso‐hydroquinone intermediate prepared by a ruthenium‐catalyzed [2+2+1+1] cycloaddition that has not been used previously in natural product synthesis. Key steps include a sterically demanding Buchwald–Hartwig amination as well as a unique C(sp3)?H amination/indole formation. Studies toward a selective desymmetrization of the meso‐hydroquinone are also reported. 相似文献
18.
Jin‐Cherng Lien Yu‐Dong Jiang Chun‐Jen Chen Sheng‐Chu Kuo Li‐Jiau Huang 《中国化学会会志》2008,55(5):1160-1165
In continuing search for novel cell differentiation agents, a series of derivatives of indole‐3‐acetic acid and indole‐3‐carboxylic acid were prepared and tested against HL‐60 cells for their differentiation and antiproliferation activities. Among them, N‐ethyl‐1‐benzylindole‐3‐carboxamide ( 14 ) was the most potent, whereas N‐methyl 1‐benzylindole‐3‐acetamide ( 5 ) and N‐methyl 1‐benzylindole‐3‐carboxamide ( 13 ) synergistically potentiated with all‐trans‐retinoic acid to induce cell differentiation as well as antiproliferation. Our results indicate that these compounds are effective cell differentiation and antiproliferation agents in combination with retinoic acid. 相似文献
19.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(52):16901-16903
Total syntheses of the monoterpenoid indole alkaloids (±)‐alstoscholarisine B and C were accomplished starting from a readily available indole‐2‐acetic ester and an α,β‐unsaturated N ‐sulfonyllactam. 相似文献
20.
Lucjan Strekowski Koen Van Aken Yuri Gulevich 《Journal of heterocyclic chemistry》2000,37(6):1495-1499
A number of 3,4,5,6‐tetrahydro‐1H‐azepino[5,4,3‐cd]indole derivatives have been synthesized starting with methyl indole‐4‐carboxylate functionalized at the 3 position. 相似文献