1694-29-7Relevant academic research and scientific papers
Synthesis, X-ray crystallographic analysis, DFT studies and biological evaluation of triazolopyrimidines and 2-anilinopyrimidines
Alsherbiny, Muhammad A.,Canfield, Peter,Fares, Mohamed,Gale, Philip A.,Guang Li, Chun,Jochmans, Dirk,Keller, Paul A.,Lewis, William,Neyts, Johan,Willis, Anthony C.
, (2021/12/21)
Inspired by the reported antiviral activity of pyrimidines and triazolopyrimidines, two series of 2-anilinopyrimidines (5a-e) and 1-aryl-[1,2,4]triazolo[4,3-a]pyrimidines (14a-k) were designed and synthesized as potential antiviral agents. X-ray crystallographic study of compounds (14d) and (14k) confirmed the structure of the desired isomer and revealed the coplanarity of the fused [1,2,4]triazolo[4,3-a]pyrimidine rings with the aryl side group. DFT studies revealed insights into the mechanism of the micro-reversible cyclisation step using DFT [B3LYP-D3(BJ)/6–31++G(d,p)]. The pharmacokinetic properties and calculation of drug likeness scores (DLS) of (5a-e) and (14a-k) suggested good traditional drug-like properties and led to the synthesis of derivatives (14a-k) which were evaluated for their anti-viral activity with the most potent derivatives subjected to cytotoxicity screening. Compounds (14a), (14c), (14e), (14f) and (14k) showed moderate to strong antiviral activity with EC50 values 38 - 186 μM. Compound (14e) (DLS = 0.29) showed the best anti-CHIKV activity (EC50 = 38 μM) and lowest cytotoxicity (CC50 > 300 μg/ml) against breast cancer cell lines, MCF-7 and MD-AMB-231 and normal cell line EA.hy926. Simplification of [1,2,4]triazolo[4,3-a]pyrimidine ring, led to series (5a-e) (DLS = 0.03 - 0.77). Derivatives (5a-d) showed fair anti-CHIKV activity (EC50 > 200 μM), while (5e) emerged as the most active antiviral agent, however the most cytotoxic.
Preparation method of dichloro dialkyl fumaronitrile
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Paragraph 0034-0039; 0050-0053; 0058-0060; 0066-0068; ..., (2021/08/25)
The preparation method comprises the following steps: I raw materials are taken as raw materials, and chlorine or N - chlorosuccinimide is used as a chlorination reagent for chlorination reaction to generate compound II. The condensation reaction of compound II with cyanoacetamide is carried out under the action of a base to give compound III. The compound III is chlororeacted with phosphorus oxychloride to give a dichloro dialkyl nicotinonitrile. The preparation method avoids the use of sulfonyl chloride as a chlorination reagent, thereby avoiding the generation of sulfur dioxide tail gas, and preventing the generated acid waste gas from corroding equipment and the like.
New benzimidazothiazole derivatives as anti-inflammatory, antitumor active agents: Synthesis, in-vitro and in-vivo screening and molecular modeling studies
El-Kerdawy, Mohamed M.,Ghali, Mariam A.,Darwish, Sara A.,Abdel-Aziz, Hatem A.,Elsheakh, Ahmad R.,Abdelrahman, Rehab S.,Hassan, Ghada S.
, p. 250 - 261 (2018/11/06)
A new series of benzimidazothiazole derivatives has been synthesized. The structure of the products was confirmed by spectroscopic techniques such as IR, NMR and mass spectroscopy. The tested compounds were evaluated for their anti-inflammatory activity e
Novel indole-thiazolidinone conjugates: Design, synthesis and whole-cell phenotypic evaluation as a novel class of antimicrobial agents
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,George, Riham F.,Abdel-Aziz, Marwa M.,Elaasser, Mahmoud M.,Abdel Gawad, Nagwa M.,Gupta, Antima,Bhakta, Sanjib,Abou-Seri, Sahar M.
, p. 49 - 60 (2018/10/20)
In connection with our research program on the development of novel anti-tubercular candidates, herein we report the design and synthesis of two different sets of indole-thiazolidinone conjugates (8a,b; 11a-d) and (14a-k; 15a-h). The target compounds were evaluated for their in vitro antibacterial and antifungal activities against selected human pathogens viz. Staphylococcus aureus (Gram positiveve), Pseudomonas aeruginosa, Escherichia coli (Gram negative), Mycobacterium tuberculosis (Acid-fast bacteria), Aspergillus fumigates and Candida albicans (fungi). Moreover, eukaryotic cell-toxicity was tested via an integrated ex vivo drug screening model in order to evaluate the selective therapeutic index (SI) towards antimicrobial activity when microbes are growing inside primary immune cells. Also, the cytotoxicity towards a panel of cancer cell lines and human lung fibroblast normal cell line, WI-38 cells, was explored to assure their safety. Compound 15b emerged as a hit in this study with potent broad spectrum antibacterial (MIC: 0.39–0.98 μg/mL) and antifungal (MIC: 0.49–0.98 μg/mL) activities, in addition to its ability to kill mycobacteria M. aurum inside an infected macrophage model with good therapeutic window. Moreover, compound 15b displayed promising activity towards resistant bacteria strains MRSA and VRE with MIC values equal 3.90 and 7.81 μg/mL, respectively. These results suggest compound 15b as a new therapeutic lead with good selectivity for further optimization and development.
Synthesis of bulky-tailed sulfonamides incorporating pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-1(5H)-yl) moieties and evaluation of their carbonic anhydrases I, II, IV and IX inhibitory effects
Fares, Mohamed,Eladwy, Radwa A.,Nocentini, Alessio,El Hadi, Soha R. Abd,Ghabbour, Hazem A.,Abdel-Megeed, Ashraf,Eldehna, Wagdy M.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, p. 2210 - 2217 (2017/03/23)
Using celecoxib as lead, two novel series of sulfonamides incorporating the pyridotriazolopyrimidine scaffold have been synthesized and evaluated in vitro as inhibitors against four relevant human (h) carbonic anhydrases (CAs, EC 4.2.1.1), the cytosolic and ubiquitous hCA I and II as well as the transmembrane hCA IV and hCA IX. Most of the reported sulfonamides acted as efficient, low micromolar inhibitors of hCAI, II and IV, whereas they displayed higher efficacy in inhibiting the tumor-associated isoform hCA IX. Many derivates herein reported showed better hCA IX versus hCA II selectivity ratios compared to celecoxib or acetazolamide. Considering isoform IX is a validated target for the diagnosis and treatment of hypoxic tumors, discovery of selective CA IX inhibitors represents a promising step to unveil more effective anticancer therapies.
Microreactor used for alpha-position hydrogen atom chlorination of alpha-dicarbonyl compound and synthesis method
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Paragraph 0017, (2016/10/20)
The invention discloses a microreactor device used for alpha-position hydrogen atom chlorination of an alpha-dicarbonyl compound and a synthesis method. The device comprises a raw material bottle, a feeding pump, a preheating or precooling pipe, a microre
Carbocations as Lewis acid catalysts: Reactivity and scope
Bah, Juho,Naidu, Veluru Ramesh,Teske, Johannes,Franzn, Johan
supporting information, p. 148 - 158 (2015/01/30)
One class of potential Lewis acids that has received negligible attention as a catalyst is the carbocation. Here we show the potential of triarylmethylium ions as highly powerful Lewis acid catalysts for organic reactions. The Lewis acidity of the triarylmethylium ion can be easily tuned by variation of the electronic properties of the aromatic rings and the catalytic activity of the carbocation is shown to correlate directly to the level of stabilization of the empty pC-orbital at the cationic carbon. The versatility of triarylmethylium ions as efficient Lewis acid catalysts for organic reactions is demonstrated in Diels-Alder, aza-Diels-Alder, conjugate addition, halogenation, epoxide rearrangement and intramolecular hetro-ene reactions.
NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts
Luo, Laichun,Meng, Lanlan,Sun, Qi,Ge, Zemei,Li, Runtao
, p. 259 - 263 (2014/01/06)
A NBS-mediated sequential one-pot synthesis of multifunctionalized thiazoles and thiophenes from 1,3-dicarbonyl compounds and mercaptonitrile salts has been developed under mild conditions. This transformation involves sequential bromination/SN
Synthesis of novel thiazolyl-pyrimidines and their anticancer activity in vitro
Shi, Hai-Bo,Li, Hai-Bo,Lu, Kong-Qin,Zhu, Xia-Re,Hu, Wei-Xiao,Pei, Wen
body text, p. 675 - 683 (2012/06/01)
A series of novel compounds 7-43 were prepared via the condensation of enaminones 4a-h and the guanidines carbonate 6a-f. The structures of these newly synthesized compounds were confirmed by 1H-NMR, MS, EA and IR. All the compounds were tested for their cytotoxic activity in vitro against human cancer cell lines including Ishikawa, A549, BEL-7404, SPC-A-01 and SGC-7901. Most of them showed moderate cytotoxic against the tested cell lines. Among them, the most potent compounds 9 and 30 exhibited more efficient activity against Ishikawa, A549. Thiazolyl-pyrimidines were synthesized by the general pyrimidine condensation of Bredereck and their in-vitro anticancer activities were evaluated. Copyright
Synthesis and anticancer evaluation of thiazolyl-chalcones
Shi, Hai-Bo,Zhang, Shi-Jie,Ge, Qiu-Fu,Guo, Dian-Wu,Cai, Chao-Ming,Hu, Wei-Xiao
body text, p. 6555 - 6559 (2010/12/19)
Thirty-seven (E)-1-(4-methyl-2-arylaminothiazol-5-yl)-3-arylprop-2-en-1- ones were synthesized via Claisen-Schmidt condensation of 1-(4-methyl-2- (arylamino)thiazol-5-yl)ethanone with the corresponding arylaldehydes. All these thiazolyl-chalcones were cha
