1477-50-5Relevant articles and documents
Improved preparation method of indole-2-formic acid as starting material of perindopril
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, (2021/07/10)
The invention discloses an improved preparation method of indole-2-formic acid by using perindopril as a starting raw material, which comprises the following steps: S1, taking 2-bromobenzaldehyde and ethyl acetate as raw materials, under the action of sodium ethoxide, carrying out Claisen-Schmidt condensation reaction to synthesize ethyl 2-bromocinnamate; s2, carrying out cyclization reaction on the ethyl 2-bromocinnamate in an amide solvent by using cuprous halide as a coupling catalyst and sodium azide as a nitrogen source to synthesize the indole-2-formic acid in one pot. According to the invention, 2-bromobenzaldehyde is used as a raw material for preparation, ethyl 2-bromocinnamate is firstly prepared, then cuprous halide is used as a coupling catalyst, sodium azide is used as a nitrogen source, cyclization reaction is carried out in an amide solvent, indole-2-formic acid is synthesized in one pot, and the HPLC content is 99% or above.
Preparation method of indole-2-formic acid derivative
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Paragraph 0030-0041, (2020/07/14)
The invention discloses a preparation method of an indole-2-formic acid derivative, wherein the preparation method comprises the steps: by using an oxazolone compound as a raw material, carrying out areaction in an organic solvent at the temperature of 70-150 DEG C under the action of alcohol, alkali and a catalyst, tracking by TLC until the raw material is completely reacted, and separating andpurifying the obtained reaction solution to obtain the indole-2-formic acid derivative. The technology is adopted, the target product indole-2-formic acid derivative is prepared by taking an oxazolonecompound as a raw material through one-pot reaction under the action of alcohol, alkali and a catalyst, so that direct conversion from an oxazolone ring to an indole ring is realized, reaction stepsand an intermediate process are reduced, and the method has the characteristics of cheap raw materials, environmental friendliness and the like, and is suitable for industrial production.
MnOx/catechol/H2O: A cooperative catalytic system for aerobic oxidative dehydrogenation of N-heterocycles at room temperature
Tang, Tao,Bi, Xiuru,Meng, Xu,Chen, Gexin,Gou, Mingxia,Liu, Xiang,Zhao, Peiqing
, (2019/12/09)
Amorphous manganese oxide doped by Na+ ion (Na-AMO) was successfully prepared and found to be an efficient heterogeneous catalyst in aerobic oxidative dehydrogenation of N-heterocycles, cooperate with catechol. Na-AMO was fully characterized by XRD, XPS BET H2-TPR, CO2-TPD FT-IR, TEM, SEM and had rich amounts of surface absorbed active oxygen species which are responsible for superior catalytic performance. The synergistic interaction between Na-AMO and catechol makes catalytic system efficient and tolerant, which offers various N-heterocycles in good to excellent yields under mild conditions.
Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions
Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa
supporting information, p. 1956 - 1960 (2020/04/10)
An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.
Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: Preparation, characterization and kinetic study
Bi, Xiuru,Tang, Tao,Meng, Xu,Gou, Mingxia,Liu, Xiang,Zhao, Peiqing
, p. 360 - 371 (2020/02/04)
OMS-2-based nanocomposites doped with tungsten were prepared for the first time and their remarkably enhanced catalytic activity and recyclability in aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute to their excellent catalytic performance. Moreover, a kinetic study was extensively performed which concluded that the dehydrogenation of 1,2,3,4-tetrahydroquinoline is a first-order reaction, and the apparent activation energy is 29.66 kJ mol-1
Design and synthesis of thiadiazolo-carboxamide bridged β-carboline-indole hybrids: DNA intercalative topo-IIα inhibition with promising antiproliferative activity
Tokala, Ramya,Sana, Sravani,Lakshmi, Uppu Jaya,Sankarana, Prasanthi,Sigalapalli, Dilep Kumar,Gadewal, Nikhil,Kode, Jyoti,Shankaraiah, Nagula
, (2020/10/27)
The conjoining of salient pharmacophoric properties directing the development of prominent cytotoxic agents was executed by constructing thiadiazolo-carboxamide bridged β-carboline-indole hybrids. On the evaluation of in vitro cytotoxic potential, 12c exhibited prodigious cytotoxicity among the synthesized new molecules 12a–k, with an IC50 50 value of 2.82 ± 0.10 μM. Besides, another compound 12a also displayed impressive cytotoxicity against A549 cell line (IC50: 3.00 ± 1.40 μM). Further target-based assay of these two compounds 12c and 12a revealed their potential as DNA intercalative topoisomerase-IIα inhibitors. Additionally, the antiproliferative activity of compound 12c was measured in A549 cells by traditional apoptosis assays revealing the nuclear, morphological alterations, and depolarization of membrane potential in mitochondria and externalization of phosphatidylserine in a concentration-dependent manner. Cell cycle analysis unveiled the G0/G1 phase inhibition and wound healing assay inferred the inhibition of in vitro cell migration by compound 12c in lung cancer cells. Remarkably, the safety profile of compound 12c was disclosed by screening against normal human lung epithelial cell line (BEAS-2B: IC50: 71.2 ± 7.95 μM) with a selectivity index range of 14.9–25.26. Moreover, Molecular modeling studies affirm the intercalative binding of compound 12c and 12a in the active pocket of topo-IIα. Furthermore, in silico prediction of physico-chemical parameters divulged the propitious drug-like properties of the synthesized derivatives.
Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway
Shen, Qing-Kun,Deng, Hao,Wang, Shi-Ben,Tian, Yu-Shun,Quan, Zhen-Shan
, p. 15 - 31 (2019/04/10)
A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.
RhCl3·3H2O-Catalyzed Regioselective C(sp2)-H Alkoxycarbonylation: Efficient Synthesis of Indole- and Pyrrole-2-carboxylic Acid Esters
Zhao, Kang,Du, Rongrong,Wang, Bingyang,Liu, Jianhua,Xia, Chungu,Yang, Lei
, p. 5545 - 5551 (2019/06/18)
The C2-selective C-H alkoxycarbonylation of indoles with alcohols and CO catalyzed by RhCl3·3H2O is disclosed that offers convenient access to diverse indole-2-carboxylic esters. The rhodium-based catalysts outperformed all other precious-metal catalysts investigated. In addition, this protocal was found applicable to the synthesis of pyrrole-2-carboxylic esters, and allowed the C-H alkoxycarbonylation in an intramolecular fashion. Preliminary mechanistic studies indicate that C-H cleavage is not likely involved in the rate-determining step, and a five-membered rhodacycle might be an intermediate involved in the reaction.
A Reusable Cobalt Catalyst for Reversible Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles
Jaiswal, Garima,Subaramanian, Murugan,Sahoo, Manoj K.,Balaraman, Ekambaram
, p. 2449 - 2457 (2019/05/10)
The development of robust catalytic systems based on base-metals for reversible acceptorless dehydrogenation (ADH) and hydrogenation of feedstock chemicals is very important in the context of ‘hydrogen storage’. Herein, we report a highly efficient reusable cobalt-based heterogeneous catalyst for reversible dehydrogenation and hydrogenation of N-heterocycles. Both the ADH and the hydrogenation processes operate under mild, benign conditions.
1H-indole-2-carboxamide derivative and preparation method and applications thereof
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Paragraph 0125; 0126, (2018/12/05)
The invention belongs to the technical field of medicine, and discloses a 1H-indole-2-carboxamide derivative of a formula (I) and a preparation method thereof. The preparation method includes the following steps: a compound of a formula (II) and sodium hydroxide are subjected to a hydrolysis reaction to synthetize a compound of a formula (III); the compound of the formula (III) and H2NR2 are subjected to an amidation reaction to synthetize a compound of a formula (IV); the compound of the formula (IV) and halogenated R1 are subjected to a nucleophilic substitution reaction to synthetize a compound of a formula (V); the compound of the formula (V) and a selectfluor are subjected to an electrophilic substitution reaction to synthetize a compound of a compound (VI), and the compound of the formula (VI) and the halogenated R1 are subjected to the nucleophilic substitution reaction to synthetize the compound of the formula (I). The 1H-indole-2-carboxamide derivative of the formula (I) is aagonist with high affinity, selectivity and activity for CB2 receptors, and can be potentially used for treating a plurality of diseases such as multiple sclerosis, autoimmune diseases, osteoporosis,arthralgia, inflammatory pain, and neurodegenerative diseases.
