41867-20-3Relevant articles and documents
Condensation of 4-chloro-2H-chromene-3-carbaldehydes and ethyl-3-aminocrotonates with p-TsOH: a facile approach for the synthesis of chromenyldihydropyridines
Madhunala, Shravani,Kurma, Siva Hariprasad,Etikala, Varsha Reddy,Bhimapaka, China Raju
, p. 2538 - 2545 (2019)
The investigated reaction of 4-chloro-2H-chromene-3-carbaldehyde 1a with ethyl 3-oxobutanoate 2a in the presence of ammonium acetate provided two compounds, 2H-chromenyldihydropyridine dicarboxylate 3a and chromenopyridine carboxylate 4a. However, the reaction of 1a with ethyl-3-aminocrotonate 5a in the presence of p-TsOH provided selectively 2H-chromenyldihydropyridine dicarboxylate 3a with very good yield. The established method was applied for the preparation of series of 2H-chromenyldihydropyridine dicarboxylates 3a–q.
Three-component synthesis of cyclic β-aminoesters using CeO2 nanoparticles as an efficient and reusable catalyst
Safaei-Ghomi, Javad,Kalhor, Sima,Shahbazi-Alavi, Hossein,Asgari-Kheirabadi, Mehrnoosh
, p. 843 - 849 (2015)
CeO2 nanoparticles were used as an efficient catalyst for the preparation of cyclic β-aminoesters by three-component reaction between primary amines, ethyl acetoacetate, and chalcones in ethanol. Atom economy, low catalyst loading, reusable catalyst, and high yields of products are some of the important features of this protocol.
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
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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.
Preparation method of 2-methoxy-6, 7-dihydro-5H-cyclopenta [b] pyridine-5-one
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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%.
Nimodipine impurity IV reference substance as well as preparation method and application thereof
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Paragraph 0064-0065, (2020/11/22)
The invention discloses a nimodipine impurity IV reference substance and a preparation method thereof. The method includes the steps that diketene, ethyl alcohol and triethylamine are taken and addedinto a container to be heated and cooled, reaction liquid is washed with water, washing liquid is discarded, anhydrous sodium sulfate is added and placed overnight, filtrate is obtained after filtration, ammonia gas is introduced into the filtrate until the filtrate is saturated, and the nimodipine impurity IV reference substance is obtained; and after the reaction is finished, m-nitrobenzaldehyde, methoxyethyl acetoacetate and ethanol are added, heating refulx is performed, the mixture is cooled and filtered, the solvent is removed through volatilization in a water bath to obtain a yellow viscous liquid, and recrystallization is carried out to obtain a yellow acicular crystal, namely the nimodipine impurity IV reference substance. The invention also discloses an application of the nimodipine impurity IV reference substance in nimodipine tablet consistency evaluation. According to the preparation method, the impurity IV can be prepared in a general analysis laboratory, special preparation equipment is not needed, the operation is simple, the purity of the obtained impurity reference substance can reach 98.4%, the purity requirement of the reference substance is met, and the preparation method can be used for consistency evaluation of the variety.
Preparation method of herbicide 3-tert-butyl-5-chloro-6-methyluracil
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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.
