78583-84-3Relevant articles and documents
Regio- and Stereoselective Chlorocyanation of Alkynes
Barrado, Alejandro G.,Zieliński, Adam,Goddard, Richard,Alcarazo, Manuel
, p. 13401 - 13405 (2017)
A variety of terminal and internal alkynes were converted regio- and stereoselectively into (Z)-3-chloroacrylonitriles by treatment with BCl3 in the presence of stoichiometric amounts of imidazolium thiocyanates. These products could be readily functionalized to provide useful building blocks, thus demonstrating the synthetic value of the method. Preliminary mechanistic studies suggest initial activation of the cationic thiocyanate by the Lewis acid, followed by electrophilic attack of the alkyne. The syn addition of a chloride to the vinyl cation intermediate and final elimination of the thiourea unit afford the desired chloroacrylonitriles.
Novel benzenesulfonamide-bearing pyrazoles and 1,2,4-thiadiazoles as selective carbonic anhydrase inhibitors
Kumar, Rajiv,Kumar, Amit,Ram, Sita,Angeli, Andrea,Bonardi, Alessandro,Nocentini, Alessio,Gratteri, Paola,Supuran, Claudiu T.,Sharma, Pawan K.
, (2021/10/05)
Two series comprising 20 novel benzenesulfonamides bearing thioureido-linked pyrazole 8 and amino-1,2,4-thiadiazole 10 were synthesized and assayed as human carbonic anhydrase (hCA) inhibitors against isoforms I and II as well as the tumor-associated isof
Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions
Sharma, Pawan K.,Kumar, Rajiv,Ram, Sita,Chandak, Navneet
supporting information, p. 1847 - 1856 (2021/04/26)
A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.
Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors
Romagnoli, Romeo,Prencipe, Filippo,Oliva, Paola,Baraldi, Stefania,Baraldi, Pier Giovanni,Schiaffino Ortega, Santiago,Chayah, Mariem,Kimatrai Salvador, Maria,Lopez-Cara, Luisa Carlota,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Bortolozzi, Roberta,Mariotto, Elena,Mattiuzzo, Elena,Viola, Giampietro
supporting information, p. 1274 - 1290 (2019/01/30)
The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.
One-pot synthesis of 2-substituted thieno[3,2-b]indoles from 3-aminothiophene-2-carboxylates through in situ generated 3-aminothiophenes
Irgashev, Roman A.,Steparuk, Alexander S.,Rusinov, Gennady L.
supporting information, (2019/09/30)
A convenient protocol for one-pot synthesis of thieno[3,2-b]indoles, bearing aromatic, thien-2-yl or styryl fragments at C-2 position, from easily accessible 5-substituted 3-aminothiophene-2-carboxylates using the Fischer indolization reaction, was develo
3-halo-3-aryl acrylonitrile and preparation method thereof
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Paragraph 0029; 0047-0049, (2018/05/16)
The invention discloses 3-halo-3-aryl acrylonitrile and a preparation method thereof. The method comprises the following steps: dissolving alkyne nitrile into a first substance comprising acetic acid,and adding alkaline metal halide salt to obtain a react
Direct synthesis of 3-halo-3-arylacrylonitriles from the addition of cyanoalkynes with alkaline metal halides
Guan, Zhipeng,Liu, Zhiwen,Shi, Wei,Chen, Hao
supporting information, p. 3602 - 3606 (2017/08/23)
An efficient synthesis of 3-halo-3-arylacrylonitrile is described from the direct addition between cyanoalkynes and inorganic alkaline metal halides such as LiCl, LiBr and KI in good to satisfactory yields. No transition metal is needed for the synthesis
Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa
Sahner, J. Henning,Empting, Martin,Kamal, Ahmed,Weidel, Elisabeth,Groh, Matthias,B?rger, Carsten,Hartmann, Rolf W.
supporting information, p. 14 - 21 (2015/04/22)
Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of
New Convenient Strategy for Annulation of Pyrimidines to Thiophenes or Furans via the One-pot Multistep Cascade Reaction of 1 H -Tetrazoles with Aliphatic Amines
Pokhodylo, Nazariy T.,Shyyka, Olga Ya.,Matiychuk, Vasyl S.,Obushak, Mykola D.
, p. 399 - 403 (2016/01/15)
A versatile, convenient, efficient and high-yield synthetic method for 2-R3,R4-amino-5-R1-6-R2-thieno[2,3-d]pyrimidin-4(3H)-ones, 2-R3,R4-amino-5-R1-6-R2-thieno[3,2-d]pyrimidin-4(3H)-ones, and benzofuro[3,2-d]pyrimidin-4(3H)-ones preparation has been developed. The reaction proceeded without using solvents and included several steps. A variety of thieno[2,3-d]pyrimidine and thieno[3,2-d]pyrimidine derivatives with substituents of different nature were obtained in high yields from substituted alkyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylates, 3-(1H-tetrazol-1-yl)thiophene-2-carboxylates, and 3-(1H-tetrazol-1-yl)benzofuran-2-carboxylate after their treatment with aliphatic amines.
SELECTIVE HDAC1 AND HDAC2 INHIBITORS
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Paragraph 0241; 0242; 0243, (2014/05/20)
Provided herein are compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with HDAC activity, particularly diseases or disorders that involve activity of HDAC1 and/or HDAC2. Such diseases include cancer, sickle-cell anemia, beta-thalassemia, and HIV.