4769-97-5Relevant academic research and scientific papers
Synthesis of model chromophores related to the gold fluorescent protein (GdFP)
Prueger, Birgit,Bach, Thorsten
, p. 1103 - 1106 (2007)
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.
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
Cheng, Yaohang,Yu, Shijie,He, Yuhang,An, Guanghui,Li, Guangming,Yang, Zhenyu
, p. 3216 - 3225 (2021/03/17)
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.
A medicine intermediate 4 - nitro indole preparation process (by machine translation)
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Paragraph 0026; 0028; 0029; 0030-0032; 0034-0036; 0038, (2019/06/13)
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)
Preparation method of pharmaceutical intermediate (4-nitroindole)
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Page/Page column 4; 5; 6, (2019/01/14)
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.
A indole compound and its preparation method and application (by machine translation)
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Paragraph 0131; 0140; 0141, (2018/10/02)
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)
A 4-nitro-indole synthesis method (by machine translation)
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Paragraph 0039; 0040; 0041; 0042; 0043; 0044; 0045; 0046, (2016/11/17)
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)
Preparation method of 4-nitroindole
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Paragraph 0024; 0028; 0032; 0036, (2017/04/12)
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.
Synthesis, in vitro and in vivo preliminary evaluation of anti-angiogenic properties of some pyrroloazaflavones
Ferlin, Maria Grazia,Conconi, Maria Teresa,Urbani, Luca,Oselladore, Barbara,Guidolin, Diego,Di Liddo, Rosa,Parnigotto, Pier Paolo
scheme or table, p. 448 - 457 (2011/02/27)
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).
Synthesis and in vitro and in vivo antitumor activity of 2-phenylpyrroloquinolin-4-ones
Ferlin, Maria Grazia,Chiarelotto, Gianfranco,Gasparotto, Venusia,Dalla Via, Lisa,Pezzi, Vincenzo,Barzon, Luisa,Palu, Giorgio,Castagliuolo, Ignazio
, p. 3417 - 3427 (2007/10/03)
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.
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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Page/Page column 29-30, (2008/06/13)
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.
