29/9/2021 News Final Thoughts on Chemistry for 6960-46-9

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Ethyl aminoindole-2-carboxylates (2), obtained by catalytic reduction of ethyl nitroindole-2-carboxylates (1) using Raney nickel, when subjected to Japp-Klingemann reaction furnish the respective indolylhydrazones (3).The latter undergo cyclization with H2SO4 to yield different isomeric benzodipyrroles (4-6).

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Properties and Exciting Facts About Ethyl 7-nitro-1H-indole-2-carboxylate

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A substituted guanidine derivative represented by the general formula: STR1 wherein R1, R2, R3 and R4 are independently a hydrogen atom, an unsubstituted alkyl group, a substituted alkyl group, a halogen atom or the like; Y1, Y2, Y3, Y4, Y5, Y 6 and Y7, which may be the same or different, are independently a single bond, –CH2 –, –O–, –CO–or the like, adjacent members of a group consisting of Y1 through Y7 being able to be taken together to represent –CH=CH–, and at least two of Y1 through Y7 being independently a group other than a single bond; Z may be absent, or one or more Zs may be present and are, the same or different, independently a substituent for a hydrogen atom bonded to any of the carbon atoms constituting the ring formed by Y1 through Y7, for example, an unsubstituted alkyl group or a substituted alkyl group, or a pharmaceutically acceptable acid addition salt thereof, is useful as a therapeutic or prophylactic agent for diseases caused by the acceleration of the sodium/proton (Na+ /H+) exchange transport system, for example, hyperpiesia, arrhythmia, angina pectoris, hypercardia, diabetes, organopathies due to ischemia or ischemia re-perfusion, troubles due to cerebral ischemia, diseases caused by cell overproliferations, and diseases caused by trouble with endothelial cells.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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CHEMICAL COMPOUNDS

The present invention relates to compounds that are a non-nucleoside reverse transcriptase inhibitors, and to processes for the preparation and use of the same. Specifically, the present invention includes methods of using such compounds in the treatment of human immunodeficiency virus infection.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Discovery of Potent Succinate-Ubiquinone Oxidoreductase Inhibitors via Pharmacophore-linked Fragment Virtual Screening Approach

Succinate-ubiquinone oxidoreductase (SQR) is an attractive target for fungicide discovery. Herein, we report the discovery of novel SQR inhibitors using a pharmacophore-linked fragment virtual screening approach, a new drug design method developed in our laboratory. Among newly designed compounds, compound 9s was identified as the most potent inhibitor with a Ki value of 34 nM against porcine SQR, displaying approximately 10-fold higher potency than that of the commercial control penthiopyrad. Further inhibitory kinetics studies revealed that compound 9s is a noncompetitive inhibitor with respect to the substrate cytochrome c and DCIP. Interestingly, compounds 8a, 9h, 9j, and 9k exhibited good in vivo preventive effects against Rhizoctonia solani. The results obtained from molecular modeling showed that the orientation of the R2 group had a significant effect on binding with the protein.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6960-46-9,Ethyl 7-nitro-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.,6960-46-9

Preparation 29: Synthesis of 7-(tetrahydro-pyran-4-ylamino)-1H-indole-2-carboxylic acidEthyl 7-nitroindole-2-carboxylate (2.5 g, 10.7 mmol) was dissolved in methanol (50 ml). 10% Pd/C (200 mg) was added, and the mixture was stirred for 1 h under hydrogen gas. The mixture was filtered through celite, and the filtrate was distilled under reduced pressure. The distillate was dissolved 1,2-dichloroethane (50 ml), and tetrahydro-4H-pyran-4-one (1.3 ml, 12.8 mmol) and sodium triacetoxyborohydride (3.4 g, 16.1 mmol) were added. The mixture was stirred for 8 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and concentrated. The residue was purified by column chromatography. Thus obtained compound was dissolved in methanol (50 ml) and tetrahydrofuran (50 ml), 1N-sodium hydroxide (43 ml, 42.8 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give the title compound (2.1 g, Yield 76%).1H-NMR (400 MHz, DMSO-d6); delta 12.87 (br s, 1H), 11.46 (s, 1H), 6.97 (d. J=2.0 Hz, 1H), 6.86 (d, J=1.6 Hz, 1H), 6.85 (s, 1H), 6.37 (m, 1H), 5.73 (br s, 1H), 3.90 (m, 2H), 3.61 (m, 1H), 3.50 (m, 2H), 2.00 (m, 2H), 1.48 (m, 2H)Mass spectrum (ESI, m/z): Calculated: 260.12, Found: 260.30

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Reference£º
Patent; Kim, Soon Ha; Kim, Hyoung Jin; Chung, Chul Woong; Park, Heui Sul; Kwak, Hyo Shin; Kim, Sung Ho; Park, Jin Gu; US2010/291533; (2010); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Downstream synthetic route of 6960-46-9

The synthetic route of 6960-46-9 has been constantly updated, and we look forward to future research findings.

6960-46-9,6960-46-9, Ethyl 7-nitro-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3: Preparation of Compound 3 (7-Nitro-1H-indole-2-carboxylic acid); The compound 2 (13.79 g, 58.88 mmol) was added into a flask (250 mL), ethanol (72.7 mL, 40 C) was added into the flask, and the solution was stirred for 5 min. Then, a solution of KOH formulated with KOH (7.25 g, 189.59 mmol) and water (17.40 g) was added into the solution, and the solution was stirred for 5 min to obtain a clear solution with red oxide color. When the solution was cooled down, a yellow-brown solid was started to precipitate. After the solution was stirred for 3 hr, hot water (295 mL) was added to dissolve the yellow-brown solids to obtain a clear solution with red oxide color. Then, 3 N of HCl was added into the solution, and a breast-yellow solid was precipitated. The solution was kept stirring unitl the precipitation of the yellow solids was stopped, and filtered. The yellow solids were washed by water, dried, and re-crystallized in ethanol to obtain a fiber-shaped light-yellow solid, compound 3 (11.57 g, 96%). mp 269-271 C (lit. 269-272 C); 1H NMR (200 MHz, DMSO-d6) delta7.35 (t, J= 8.0 Hz, 1H, ArH), 7.40 (d, J= 2.0 Hz, 1H, ArH), 8.22 (d, J= 7.8 Hz, 1H, ArH), 8.27 (dd, J= 0.8, 8.0 Hz, 1H, ArH), 11.16 (s, 1H, NH); 13C NMR (50 MHz, acetone-d6) delta109.6, 110.0, 120.6, 122.3, 130.1, 131.3, 131. 8, 134.0, 161.6; MS (EI) m/z 206 (M+, 100%), 188 (M-18, 65%), 142 (M-64, 49%), 114 (M-92, 43%).

The synthetic route of 6960-46-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Purzer Pharmaceutical Co., Ltd.; EP2366687; (2011); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles