1222-57-7Relevant academic research and scientific papers
A multi pathway coupled domino strategy: I2/ TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization
Feng, Lei,Li, Shichen,Ma, Chen,Wang, Xinfeng,Wang, Yishou,Yao, Yiming
, p. 5919 - 5927 (2022/03/31)
I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.
Design, synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives as selective COX-2 inhibitors
Abdel-Rahman, Hamdy M.,Ali, Mohammed R. A.,Amin, Noha H.,Elsaadi, Mohammed T.,Ismael, Ahmed S.
, (2021/10/22)
Three new series of methylsulfonyl-containing imidazo[1,2-a]pyridines 8a-d, 9a-d and 10a-d were designed and synthesized. Characterization of the chemical structure of these new compounds was performed using spectral and elemental analyses. The synthesized derivatives were tested for their ability to inhibit COX-1 and COX-2 isozymes in addition to their in vivo anti-inflammatory activity. The pyrazoline derivative 9a possessed the highest selectivity index among all compounds regarding COX-2 isozyme (SI = 39) and was almost three folds higher than celecoxib (SI = 13.76) with good in vivo anti-inflammatory activity (% edema inhibition = 11.16–32.64). Compound 10c showed the highest inhibitory activity towards COX-2 isozyme (IC50 = 1.06 μM) and it was the most potent anti-inflammatory derivative (% edema inhibition = 15.04–42.35) with ED50 value of 69.46 μmol/Kg which was approximately one and a half fold more potent than celecoxib (ED50 = 104.88 μmol/Kg). Also, the most potent anti-inflammatory compounds 9a, 9d, 10c and 10d were subjected to ulcerogenic liability and histopathological examinations. Compounds 9d and 10c showed ulcerogenic liability (% ulcerated area = 0.07 and 0.01, respectively) and histopathological changes close to celecoxib. Finally, molecular docking and computational prediction of physicochemical parameters were performed for the prepared compounds to support the biological results.
Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water
Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong
supporting information, p. 6322 - 6329 (2021/09/10)
A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.
Metal-free, Tf2NH-catalyzed 1, 6-conjugate addition of imidazopyridine to para-quinone methides: Easy access to C3-functionalized triarylmethane imidazopyridine
Khonde, Nilesh S.,Said, Madhukar S.,Sabane, Jagjivan K.,Gajbhiye, Jayant M.,Kumar, Pradeep
supporting information, (2021/10/30)
An inexpensive and commercially available Tf2NH-catalyzed 1,6-conjugate addition of imidazopyridine (IMPY) heterocycles to para-quinone methides (p-QMs) is reported. The present transformation provides a diverse class of C3-functionalized triarylmethanes heterocyclic derivatives of imidazopyridine. These metal-free transformations provided a very broad substrate scope of conjugate addition product with a high yield up to 97% within a short duration.
Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles
Chitrakar, Ravi,Rawat, Deepa,Sistla, Ramakrishna,Subbarayappa, Adimurthy,Vadithe, Lakshma Nayak
supporting information, (2021/08/13)
We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.
Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation
Liu, Kai-Jian,Wang, Zheng,Lu, Ling-Hui,Chen, Jin-Yang,Zeng, Fei,Lin, Ying-Wu,Cao, Zhong,Yu, Xianyong,He, Wei-Min
, p. 496 - 500 (2021/01/28)
A safe, practical and eco-friendly method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated oxygenation of sulfides at ambient temperature under transition-metal-, additives-free and minimal solvent conditions. The synergistic catalytic efforts between CF3SO2Na and 2-butoxyethyl ether represents the key promoting factor for the reaction. This journal is
Imidazopyridine compound, pharmaceutical composition containing the same, and preparation method and application thereof (by machine translation)
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Paragraph 0062-0066; 0266-0270, (2020/05/01)
Specifically discloses a pharmaceutical composition containing the compound and a pharmaceutically acceptable salt or a pharmaceutically acceptable solvate [1,2 - a] of the compound, and the preparation method, comprises the following steps of inhibiting, protein selectivity, drug effect strong STAT3 patent medicine, safety and the like, and the like . is particularly suitable for preventing and, or treating tumor growth and metastasis as well as pharmaceutical composition and pharmaceutical acceptable salt or pharmaceutically acceptable salt or pharmaceutically acceptable solvate of the compound in preparing STAT3 high-expression cell abnormal proliferation, form change and exercise function hyperthyroidism, and other related diseases / and are disclosed in the present invention. (by machine translation)
Metal-free benzoylation of imidazoheterocycles by oxidative decarboxylation of arylglyoxylic acids
Jaspal, Sonam,Shinde, Vikki N.,Meena, Neha,Nipate, Dhananjay S.,Rangan, Krishnan,Kumar, Anil
supporting information, p. 9072 - 9080 (2020/11/27)
A simple and straightforward approach has been realized for the direct benzoylation of imidazoheterocycles by oxidative decarboxylation of arylglyoxylic acids in the presence of K2S2O8 as an oxidant. Various functional groups were tolerated on both imidazoheterocycles and arylglyoxylic acids and a wide range of C5-benzoyl-imidazoheterocycles were obtained in good to high yields (50-84%). Radical trapping experiments confirmed the involvement of the radical pathway. The developed protocol is amenable for a scale-up reaction. This journal is
A simple and efficient route to 2-arylimidazo[1,2-a]pyridines and zolimidine using automated grindstone chemistry
Das, Dharmendra,Bhutia, Zigmee T.,Panjikar, Padmini C.,Chatterjee, Amrita,Banerjee, Mainak
supporting information, p. 4099 - 4107 (2020/09/09)
A green and efficient mechanochemical method for the synthesis of a series of 2-arylimidazo[1,2-a]pyridines was developed using an electrical grinder. I2 catalyzed mechanochemical grinding facilitates the cyclocondensation reaction between various aryl methyl ketones and 2-aminopyridines to afford 2-arylimidazo[1,2-a]pyridines in good yields at ambient temperature. The method was successfully used for the gram-scale synthesis of a marketed drug, zolimidine. The noticeable advantages of this environmentally sustainable protocol include mild conditions, simple instrumentation, inexpensive catalyst, atom economy, short reaction time etc.
Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
supporting information, p. 433 - 438 (2020/02/13)
The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
