- Synthesis of model chromophores related to the gold fluorescent protein (GdFP)
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The two model chromophores 2 and 3 for the core 1 of the gold fluorescent protein (GdFP) were synthesized from commercially available 2-methyl-3- nitroaniline (4) in six synthetic steps and overall yields of 13% and 8%, respectively. The key step of the sequence is the chemoselective, reductive introduction of the amino group after assembly of the Z-configured 5-(indol-3-ylmethylene)imidazolin-4-one skeleton of the chromophore. Compound (Z)-2 was shown to undergo a light-initiated E/Z-isomerization, which allows access also to its E-isomer. Georg Thieme Verlag Stuttgart.
- Prueger, Birgit,Bach, Thorsten
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Read Online
- C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysisvs.Pd(ii) catalysis
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Efficient C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles have been developed. The former route enables C4-arylation in a highly efficient and mild manner and the latter route provides an alternative straightforward protocol for synthesis of C2/C4 disubstituted indoles. The mechanism studies imply that the different reaction pathways were tuned by the distinct acid additives, which led to either the Pd(i)-Pd(ii) pathway or Pd(ii) catalysis.
- Cheng, Yaohang,Yu, Shijie,He, Yuhang,An, Guanghui,Li, Guangming,Yang, Zhenyu
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p. 3216 - 3225
(2021/03/17)
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- A medicine intermediate 4 - nitro indole preparation process (by machine translation)
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The present invention discloses a pharmaceutical intermediate 4 - nitro indole preparation process, which belongs to the field of pharmaceutical intermediates. The invention relates to 2 - methyl - 3 - nitroaniline with the original carboxylic acid triethyl ester as raw material, in the sulfonic acid type cation exchange resin and common under the catalysis of the sodium tartrate, for 95 - 105 °C lower, reaction generating N - (2 - methyl - 3 - nitrophenyl) b [...] imine, N - (2 - methyl - 3 - nitrophenyl) b oxygen radical armor imine with strong alkali and diethyl oxalate phosphite to produce 4 - nitro indole. The invention two-step process of 4 - nitro indole, intermediate does not need purification, simplifies the process, and avoiding the loss of the product; at the same time the process of the invention, simple post-treatment, the product has high purity, the purification process of product loss, high yield. (by machine translation)
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Paragraph 0026; 0028; 0029; 0030-0032; 0034-0036; 0038
(2019/06/13)
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- A indole compound and its preparation method and application (by machine translation)
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The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)
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Paragraph 0131; 0140; 0141
(2018/10/02)
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- Preparation method of pharmaceutical intermediate (4-nitroindole)
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The invention discloses a preparation method of a pharmaceutical intermediate (4-nitroindole). The preparation method specifically comprises the following steps of firstly, using para-methylbenzenesulfonic acid, citric acid and cerium nitrate as raw materials, and reacting with an alkaline solution, so as to obtain a rare earth cerium-coordinated complex containing para-methylbenzenesulfonic acidand citric acid; using the rare earth cerium-coordinated complex as a catalyst to catalyze 2-methyl-3-nitroaniline and triethyl orthoformate to react, so as to obtain N-(2-methyl-3-nitrobenzo)ethoxymethylamine, and mixing with diethyl oxalate and potassium acetate, so as to obtain a target product. The preparation method has the advantages that the reaction conditions are mild; the yield rate of the prepared product is high.
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Page/Page column 4; 5; 6
(2019/01/14)
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- Preparation method of 4-nitroindole
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The invention discloses a preparation method of 4-nitroindole. The preparation method comprises the following steps: nitrating 4-methoxyphenylhydrazine hydrochloride to prepare 3-nitryl-4-methoxyphenylhydrazine hydrochloride, then enabling the 3-nitryl-4-methoxyphenylhydrazine hydrochloride to react with acetaldehyde under the catalysis of a catalyst to prepare 5-methoxyl-4-nitroindole, and finally removing methoxyl to obtain the required 4-nitroindole. The reaction process is as shown in the following figure. According to the method, a ternary catalyst system is used, so that the reaction conversion rate is high, and the selectivity is high. Furthermore, reaction conditions for the preparation method are mild, and the reaction cost is relatively low; the preparation method has relatively high industrial production prospect.
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Paragraph 0024; 0028; 0032; 0036
(2017/04/12)
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- A 4-nitro-indole synthesis method (by machine translation)
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The invention discloses a 4-nitro-indole synthesis method, which belongs to the field of chemical synthesis, in order to 2-methyl-3-nitroaniline with the original a acid tri-ethyl ester in 100 °C under catalysis and benzoic acid, the reaction 1.5-2h generating N-(2-methyl-3-nitrophenyl) b oxygen radical armor imine, N-(2-methyl-3-nitrophenyl) b oxygen radical armor imine with sodium ethoxide and oxalic acid bis ethyl ester in 40 °C reaction 1.5h, to produce 4-nitro indole crude product, 4-nitro indole crude product after recrystallizing and sublimation reaction to obtain the 4-nitro-indole. The method of the invention in the prior art to the process parameters on the basis of optimizing one by one, the overall yield of the reaction, reduce the reaction time, improve the synthesis economic benefits. (by machine translation)
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Paragraph 0039; 0040; 0041; 0042; 0043; 0044; 0045; 0046
(2016/11/17)
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- Synthesis, in vitro and in vivo preliminary evaluation of anti-angiogenic properties of some pyrroloazaflavones
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This work investigated the in vitro and in vivo anti-angiogenic activity of some pyrroloazaflavones, exactly 2-phenyl-1H-pyrrolo[2,3-h]quinolin-4(7H)ones, with vinblastine as reference compound. Growth inhibitory activity, migration, and capillary-like structures formation were determined in human umbilical vein endothelial cell cultures, and Matrigel plug assay was carried out to evaluate in vivo effects on angiogenesis. Collectively, our results indicate that some pyrroloazaflavone derivatives, at non-cytotoxic concentrations and like vinblastine are able: (i) to exert in vitro anti-angiogenic activity and (ii) to counteract in vitro and in vivo the pro-angiogenic effects of fibroblast growth factor-2 (FGF-2).
- Ferlin, Maria Grazia,Conconi, Maria Teresa,Urbani, Luca,Oselladore, Barbara,Guidolin, Diego,Di Liddo, Rosa,Parnigotto, Pier Paolo
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scheme or table
p. 448 - 457
(2011/02/27)
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- NOVEL TETRAYDROSPIRO{PIPERIDINE-2,7’ -PYRROLO[3,2-b]PYRIDINE DERIVATIVES AND NOVEL INDOLE DERIVATIVES USEFUL IN THE TREATMENT OF 5-HT6 RECEPTOR -RELATED DISORDERS
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The present invention relates to compounds of formula (I): Formula (I) wherein U, P, W1, W2, W3, v, Y, Z, Rm, and Rm’ are as described herein, to pharmaceutical compositions comprising the compounds, to processes for their preparation, as well as to the use of the compounds for the preparation of a medicament against 5-HT6 receptor-related disorders.
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Page/Page column 29-30
(2008/06/13)
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- Synthesis and in vitro and in vivo antitumor activity of 2-phenylpyrroloquinolin-4-ones
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In our search for potential new anticancer drugs, we designed and synthesized a series of tricyclic compounds containing the antimitotic 2-phenylazaflavone chromophore fused to a pyrrole ring in a pyrroloquinoline structure. Compounds 8, 18, 19, 22, 23, 25 and 26, when tested against a panel of fourteen human tumor cell lines, showed poor in vitro cytotoxic activity, whereas 20, 21 and 24 showed significant activity (IC50 0.7 to 50 μM). Steroid hormone-sensitive ovary, liver, breast and adrenal gland adenocarcinoma cell lines displayed the highest sensitivity (IC50 0.7 to 8 μM). Compound 24 blocked cells in the G2/M phase of the cell cycle and induced a significant increase in apoptotis. Compounds 20, 21 and 24 proved to alter microtubule assembly and stability, displaying a cytoplasmic microtubule network similar to that caused by Vincristine. In vivo, administration of compound 24 to Balb/c mice inhibited the growth of a syngenic hepatocellular carcinoma.
- Ferlin, Maria Grazia,Chiarelotto, Gianfranco,Gasparotto, Venusia,Dalla Via, Lisa,Pezzi, Vincenzo,Barzon, Luisa,Palu, Giorgio,Castagliuolo, Ignazio
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p. 3417 - 3427
(2007/10/03)
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- 4-indole derivatives as serotonin agonists and antagonists
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The present invention relates to compounds of the formula
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- Simple one step syntheses of indole-3-acetonitriles from indole-3-carboxaldehydes
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One step conversion method of indole-3-carboxaldehydes into indole-3-acetonitriles is developed. Applying the method, 4-nitro- (7 a), 4-phenyl-(7 b), 4-iodo- (7 c), 4-methoxy- (7 d), and 4-benzyloxyindole-3-acetonitrile (7 e) are available in two steps from indole-3-carboxaldehyde (4).
- Yamada, Fumio,Hashizume, Tomoko,Somei, Masanori
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p. 509 - 516
(2007/10/03)
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- Palladium-Catalyzed Synthesis of Indoles by Reductive N-Heteroannulation of 2-Nitrostyrenes
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A palladium-phosphine catalyzed reductive N-heteroannulation of 2-nitrostyrenes, in the presence of carbon monoxide, producing indoles has been developed. Indoles were obtained, in moderate to excellent yield, from substituted 2-nitrostyrenes having either electron-withdrawing (NO2 and CO2-Me) or electron-donating (Br, OH, Me, OMe, and OTf) substituents on the aromatic ring. Best results were obtained using palladium diacetate (6 mol percent) together with triphenylphosphine (24 mol percent) as the catalytic system, under 4 atm of carbon monoxide in acetonitrile at 70 °C. Other palladium(II) and palladium(0) complexes also catalyze the reaction.
- So?derberg, Bjo?rn C.,Shriver, James A.
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p. 5838 - 5845
(2007/10/03)
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- New total synthesis of (±)-chuangxinmycin
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(±)-4'-Iodoindolmycenate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 16 with retention of C2-stereochemistry in (±)-6. Palladium-catalysed cyclisation of indolyl iodide and the internal C2 thiol group of the substrate (±)-17 derived from (±)-16 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1).
- Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
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p. 1805 - 1808
(2007/10/03)
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- Protein Kinase C Modulators. Indolactams. 2. Alkylation of 4-Nitroindole by Grignard Reagents. Synthesis of (-)-7-Octylindolactam V
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A method for the C-alkylation of 4-nitroindole at the 5 and 7 positions by alkyl Grignard reagents has been developed.The 4-nitro-7-octylindole thus prepared has been used as a starting material for the synthesis of the lyngbyatoxin analog, (-)-7-octylindolactam V.
- Quick, James,Saha, Bijali
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p. 8553 - 8556
(2007/10/02)
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- 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
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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
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p. 2783 - 2804
(2007/10/02)
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- SIMPLE SYNTHESES OF 1,3,4,5-TETRAHYDROPYRROLOQUINOLINE AND 5-HYDROXY-4-NITROINDOLE (SYNTHETIC STUDY FOR INDOLES HAVING A NITROGEN CONTAINING FUNCTIONAL GROUP AT THE 4-POSITION)
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A simple four (or three) step synthesis method for 1,3,4,5-tetrahydropyrroloquinoline (6) from indole-3-carboxaldehyde (9) is developed.A single step preparation of 5-hydroxy-4-nitroindole (8) by the oxidation of 4-aminoindole (16) is also reported.
- Hamabuchi, Shin,Hamada, Hirokazu,Hironaka, Akiko,Somei, Masanori
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p. 443 - 448
(2007/10/02)
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- Synthesis of Indoles via Ring Closure of 2-Alkylnitroaniline Derivatives.
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A variety of nitroindoles have been prepared from imidate, amidine, and sec-anilide derivatives of 2-alkyl-3- or 5-nitroanilines by a base-induced cyclization promoted by dialkyl oxalates.It is shown that essentially the same procedure also can be used to synthesize the corresponding nitroindole-3-glyoxylates in one simple operation.The synthetic potential is discussed and a mechanism is proposed.
- Bergman, Jan,Sand, Peter
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p. 6085 - 6112
(2007/10/02)
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- Synthesis of 2'-deoxyribofuranosyl indole nucleosides related to the antibiotics SF-2140 and neosidomycin
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The 2'-deoxyribofuranose analog of the naturally occurring antibiotics SF-2140 and neosidomycin were prepared by the direct glycosylation of the sodium salts of the appropriate indole derivatives, with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose. Thus, treatment of the sodium salt of 4-methoxy-1H-indol-3-ylacetonitrile with 5 provided the blocked nucleoside, 4-methoxy-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1 -indol-3-ylacetonitrile, which was treated with sodium methoxide to yield the SF-2140 analog, 4-methoxy-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetoni rile. The neosidomycin analog was prepared by treatment of the sodium salt of 1H-indol-3-ylacetonitrile with 5 to obtain the blocked intermediate 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)-1H-3-ylacet nitrile followed by sodium methoxide treatment to give 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetonitrile and finally conversion of the nitrile function of 7b to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3-ylacetamide. In a similar manner, indole and several other substituted indoles including 1H-indole-4-carbonitrile, 4-nitro-1H-indole, 4-chloro-1H-indole-2-carboxamide and 4-chloro-1H-indole-2-carbonitrile were each glycosylated and deprotected to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-4-carbonitrile, 4-nitro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole, 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carboxami e and 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-2-carbonitr le, respectively. The 2'-deoxyadenosine analog in the indole ring system was prepared for the first time by reduction of the nitro group of 11c using palladium on carbon thus providing 4-amino-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole (1,3,7-trideaza-2'-deoxyadenosine).
- Girgis,Cottam,Robins
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p. 361 - 373
(2007/10/02)
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- Some Observations on the Formation of 1-Hydroxyindoles in the Leimgruber-Batcho Indole Synthesis
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The factors influencing the formation of 1-hydroxyindoles in the catalytic hydrogenation of β-dimethylamino-2-nitrostyrenes (Leimgruber-Batcho indole synthesis) have been investigated.Significant amounts of 1-hydroxyindoles were obtained only when the β-dimethylamino-2-nitrostyrene was substituted with an electron-withdrawing group at the 5 or 6 position.The proportion of 1-hydroxyindole formed relative to the normal indole product was found to increase as both the amount of catalyst and hydrogen pressure were decreased.
- Clark, Robin D.,Repke, David B.
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p. 121 - 125
(2007/10/02)
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- HETEROGENEOUS-CATALYTIC E. FISCHER REACTION XIV. EFFECT OF ELECTRONIC FACTORS IN THE HETEROGENEOUS-CATALYTIC E. FISCHER REACTION
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The effect of electronic factors on the heterogeneous-catalytic E.Fischer reaction was studied for the case of methoxy- and nitro-substituted arylhydrazones.It was shown that the presence of the methoxy groups in all probability increases the basicity of the respective hydrazone and facilitates adsorption of the active centers of the catalyst.In this case indoles are obtained with high yields.The presence of nitro groups hinder the adsorption of the hydrazone on the catalyst and as a result leads to a decrease in the yield of indole.
- Suvorov, N. N.,Shkil'kova, V. N.,Podkhalyuzina, N. Ya.
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p. 2117 - 2120
(2007/10/02)
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- SYNTHESIS OF 4-SUBSTITUTED INDOLES FROM o-NITROTOLUENES
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A facile two- or three-step transformation of o-nitrotoluenes into 4-substituted indoles is described.Treatment of o-nitrotoluenes 1 with DMF acetal, or sometimes more advantageously with tris(N,N-dimethylamino)methane, affords β-(N,N-dimethylamino)styrenes 2 which are readily converted too-nitrophenylacetaldehyde semicarbazones 3 without isolation.Reduction of either 2 or 3 affords 4-substituted indoles 4.Use of the very insoluble semicarbazones results in vastly superior yields of 4 by minimizing completing bimolecular condensation reactions during reduction.This new procedure has been applied to efficiently and conveniently prepare a series of 4-substituted indoles 4.
- Kruse, Lawrence I.
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p. 1119 - 1124
(2007/10/02)
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