626-34-6Relevant articles and documents
Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method
Hosseininasab, Fatemeh Sadat,Memarian, Hamid Reza
, (2022/01/11)
Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.
HISTONE ACETYLTRANSFERASE (HAT) INHIBITOR AND USE THEREOF
-
Paragraph 0859-0860, (2021/02/25)
The present invention relates to a histone acetyltransferase (HAT) inhibitor. Provided are a compound represented by general formula I, a pharmaceutically acceptable salt, a stereoisomer, an enantiomer, a diastereomer, an atropisomer, a racemate, a polymorph, a solvate or an isotope-labeled compound (including deuterium substitution) thereof, a preparation method therefor, a pharmaceutical composition comprising the same, and use thereof in the treatment of various HAT-related diseases or conditions.
Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines
Han, Chunyu,Tian, Xianhai,Zhang, Huili,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 4764 - 4768 (2021/06/30)
A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.
Synthesis and Biological Activities of Nicotinaldehyde Based 1,4-Dihydropyridinedicarboxylates
Hariprasad, K. S.,Prakasham, R. S.,Praveena, G.,Raju, B. China,Ramya, S.,Suchitra Rani, K.,Tiwari, A. K.,Zehra, A.
, p. 1335 - 1340 (2021/12/23)
Abstract: 1,4-Dihydropyridinecarboxylates were prepared by the reaction of nicotinaldehydes with aminocrotonoates in the presence of p-TsOH at room temperature. The prepared compounds were evaluated for their anti-microbial, free-radical scavenging and α-glucosidase inhibitory activities. Compounds diethyl 2,6-diphenyl-4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(2-chloro-5-(4-fluorophenyl)pyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate were identified as potent anti-fungal agents. The compounds diethyl 2,6-dimethyl-4-(pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate, dimethyl 4-(2-chloropyridin-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 2,6-dimethyl-4-(pyridin-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate were identified as ABT?+ free radical scavengers. The compounds diethyl 4-(2-chloro-5-phenylpyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate and diethyl 4-(2-chloro-5-phenylpyridin-3-yl)-2,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate denoted α-glucosidase inhibitory activity.
Chiral diphosphine ligand rhodium complex containing tetra (3, 5-bis (trifluoromethylphenyl) boron anions and preparation method and application thereof
-
Paragraph 0056-0065, (2021/10/27)
The invention relates to a chiral diphosphine ligand rhodium complex containing tetra (3, 5-bis (trifluoromethylphenyl) boron anions and a preparation method and application thereof. Specifically, the high-stability chiral diphosphine ligand rhodium complex containing BArF anions can be obtained by complexing a chiral diphosphine ligand with a rhodium salt and then carrying out anion exchange with NaBArF. The complex can efficiently catalyze an asymmetric catalytic hydrogenation reaction of beta-dehydroamino acid ester to prepare a beta-amino acid ester derivative with high optical purity, so that a synthetic method suitable for industrialization is provided for optically pure beta-amino acid and beta-amino alcohol, and the complex has a good application prospect.
On the enantioselective phosphoric-acid-catalyzed hantzsch synthesis of polyhydroquinolines
Bonne, Damien,Bressy, Cyril,Bugaut, Xavier,Constantieux, Thierry,Jean, Marion,Lemaitre, Clément,Quinonero, Ophélie,Rodriguez, Jean,Roussel, Christian,Vanthuyne, Nicolas
supporting information, p. 3394 - 3398 (2021/05/29)
A reinvestigation of a chiral phosphoric-acid-catalyzed four-component Hantzsch enantioselective synthesis of polyhydroquinolines reported in 2009 is presented. In our hands, when the reaction was performed with fidelity to the original report using a chiral enantiopure phosphoric acid catalyst, no enantioselectivity was observed. Unlike in the original report, enantioselectivity results are backed by baseline separation of the enantiomers by HPLC analyses on chiral stationary phase with UV and chiroptical detection.
Preparation method of 2-methoxy-6, 7-dihydro-5H-cyclopenta [b] pyridine-5-one
-
Paragraph 0006; 0040-0046; 0080-0085; 0119-0124; 0158-0163, (2020/08/22)
The invention relates to a preparation method of 2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-5-one. According to the preparation method, ethyl acetoacetate is used as a starting raw material, and anovel target product 2-methoxy-6, 7-dihydro-5H-cyclopenta[b]pyridine-5-one is prepared through nine steps of reactions including dehydration, addition, cyclization, chlorination, bromination, substitution, cyclization again, decarboxylation and etherification. The preparation method of the novel target product is simple and efficient. The purity of the novel target product prepared by the methoddisclosed by the invention reaches over 99.0%.
Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions
Chandran,Pise, Ashwini,Shah, Suraj Kumar,Rahul,Suman,Tiwari, Keshri Nath
supporting information, p. 6557 - 6561 (2020/08/24)
A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method.
Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil
-
Paragraph 0010; 0024-0027, (2019/05/02)
The invention discloses a preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil. The method comprises the steps that a compound acetoacetic ester is taken as a raw material to react with an ammonia source to generate 3-amino-2-butenoic acid ethyl ester, the 3-amino-2-butenoic acid ethyl ester is reacted with tert-butylisocyanate to generate an intermediate, and the 3-tert-butyl-5-chloro-6-methyluracil is obtained after chlorination is conducted on the intermediate. The method has the advantages that the obtaining of the raw material is easy, the technology is brief, the method is economical and environmentally friendly, and the method is suitable for industrial production.
Unsymmetric dihydropyridines bearing 2-pyridyl methyl carboxylate as modulators of P-glycoprotein; Synthesis and biological evaluation in resistant and non-resistant cancer cells
Nejati, Maryam,Sadeghpour, Hossein,Ranjbar, Sara,Javidnia, Katayoun,Edraki, Najmeh,Saso, Luciano,Firuzi, Omidreza,Miri, Ramin
, p. 603 - 614 (2019/08/06)
Multi-drug resistance (MDR) in cancer cells is often associated with overexpression of P-glycoprotein (P-gp or ABCB1 or MDR1); therefore, modulators of this transporter might be helpful in overcoming MDR. In this study, 16 novel unsymmetrical dihydropyridine (DHP) derivatives bearing 2-pyridyl methyl carboxylate at C3 and a nitroimidazole or nitrophenyl ring at C4 positions of the DHP ring were synthesized. Their cytotoxicity was tested against four human cancer cells by MTT assay. The reversal capacity of MDR was examined in P-gp overexpressing cells (MES-SA/DX5) by measuring the alteration of doxorubicin's IC50 and performing flow cytometric determination of intracellular rhodamine 123 accumulation. The calcium channel blocking (CCB) activity, as a side effect of DHPs, was tested on the ileum of a guinea pig. Molecular docking was performed to explain the binding mode of compounds. Two derivatives, 4a and 4c, containing 4-nitrophenyl at C4 and possessing methyl (4a) and iso-propyl (4c) carboxylates at the C5 position of DHP core demonstrated superior cytotoxic and MDR reversal activities and lower CCB effect. Docking analysis confirmed the importance of the 4-nitrophenyl ring for P-gp inhibitory activity. Some of the synthesized DHP derivatives with considerable MDR reversal capacity could be promising compounds for further discovery of useful agents for management of drug resistant cancer.
