38449-13-7Relevant articles and documents
Photoredox Cyclization of N-Arylacrylamides for Synthesis of Dihydroquinolinones
Liu, Zhaosheng,Zhong, Shuai,Ji, Xiaochen,Deng, Guo-Jun,Huang, Huawen
supporting information, p. 349 - 353 (2021/12/27)
Metal- and additive-free photoredox cyclization of N-arylacrylamides is herein reported that provides a concise access to the formation of dihydroquinolinones. In this protocol, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. This reaction system features exclusive 6-endo-trig cyclization selectivity with a generally good yield of a range of functionalized dihydroquinolinones and dihydrobenzoquinolinones. Mechanistical studies reveal the feasibility of both 1,3-H shift and intersystem crossing of the diradical intermediate.
RhIII-Catalyzed C-H (Het)arylation/Vinylation of N-2,6-Difluoroaryl Acrylamides
Wang, Huai-Wei,Qiao, Yu-Han,Wu, Jia-Xue,Wang, Qiu-Ping,Tian, Meng-Xin,Li, Yong-Fei,Yao, Qing-Xia,Li, Da-Cheng,Dou, Jian-Min,Lu, Yi
supporting information, p. 656 - 662 (2021/02/01)
RhIII-catalyzed sp2 C-H cross-coupling of acrylamides with organoboron reactants has been accomplished using a commercially available N-2,6-difluoroaryl acrylamide auxiliary. A broad range of aryl and vinyl boronates as well as a variety of heterocyclic boronates with strong coordinating ability can serve as the coupling partners. This transformation proceeds under moderate reaction conditions with excellent functional group tolerance and high regioselectivity.
Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with N-Sulfonyl Amides via C-H Activations
Sun, Manman,Chen, Weida,Xia, Xiangyu,Shen, Guodong,Ma, Yongmin,Yang, Jianguo,Ding, Hanfeng,Wang, Zhiming
supporting information, p. 3229 - 3233 (2020/04/10)
A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp2)-H activation, allylic C(sp3)-H activation, and homoallylic C(sp3)-H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.
Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes
Bouillon, Jean-Philippe,Brégent, Thibaud,Poisson, Thomas
supporting information, p. 7688 - 7693 (2020/10/09)
The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.
Synthesis method and applications of N heteroatom polysubstituted benzoquaternary cycloketone
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Paragraph 0075; 0081-0084, (2020/03/12)
The invention discloses an N heteroatom polysubstituted benzoquaternary cycloketone synthesis method. According to the invention, the synthetic route starts from a known aniline compound A, the hundred g-scale preparation can be achieved, the yield can ac
N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.
supporting information, p. 141 - 156 (2019/03/17)
The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.
Synthesis and discovery of 18β-glycyrrhetinic acid derivatives inhibiting cancer stem cell properties in ovarian cancer cells
Li, Xiaojing,Liu, Yihua,Wang, Na,Liu, Yuyu,Wang, Shuai,Wang, Hongmin,Li, Aihua,Ren, Shaoda
, p. 27294 - 27304 (2019/09/12)
Despite advances in ovarian cancer treatment, the five-year overall survival rate is less than 30% with the presence of cancer stem cells (CSCs). To develop CSC-targeting therapy, a series of 18β-glycyrrhetinic acid (GA) derivatives containing cinnamamide moiety have been designed, synthesized, and screened for their antiproliferative activity in SKOV3 and OVCAR3 cells. Most of the compounds exhibited stronger antiproliferative activity than GA, and compound 7c was the most active one. Further biological studies showed that compound 7c could induce apoptosis and suppress migration. In addition, compound 7c could not only observably decrease the colony formation and sphere formation ability, but also significantly reduce the CD44+, CD133+, and ALDH+ subpopulation in SKOV3 and OVCAR3 cells. In conclusion, these results indicate that compound 7c is a promising anti-CSC agent for further anti-ovarian cancer studies.
Co(iii)-catalyzed: Z -selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene
Zhao, Tingxing,Qin, Dekun,Han, Weiguo,Yang, Shiping,Feng, Boya,Gao, Ge,You, Jingsong
supporting information, p. 6118 - 6121 (2019/06/03)
A Co(iii)-catalyzed direct oxidative C-H/C-H cross-coupling reaction of acrylamides with triisopropylsilylacetylene is presented. It is applicable to unsubstituted, internal and terminal acrylamides with a broad functionality tolerance. The feasibility of
Synthesis and biological evaluation of celastrol derivatives as anti-ovarian cancer stem cell agents
Li, Xiaojing,Ding, Jie,Li, Ning,Liu, Wenxia,Ding,Zheng, Huijuan,Ning, Yanyan,Wang, Hongmin,Liu, Renmin,Ren, Shaoda
, p. 667 - 679 (2019/07/05)
Ovarian cancer is associated with a high percentage of recurrence of tumors and resistance to chemotherapy. Cancer stem cells (CSCs) are responsible for cancer progression, tumor recurrence, metastasis, and chemoresistance. Thus, developing CSC-targeting therapy is an urgent need in cancer research and clinical application. In an attempt to achieve potent and selective anti-CSC agents, a series of celastrol derivatives with cinnamamide chains were synthesized and evaluated for their anti-ovarian cancer activities. Most of the compounds exhibited stronger antiproliferative activity than celastrol, and celastrol derivative 7g with a 3,4,5-trimethoxycinnamamide side chain was found to be the most potent antiproliferative agent against ovarian cancer cells with an IC50 value of 0.6 μM. Additionally, compound 7g significantly inhibited the colony formation ability and reduced the number of tumor spheres. Furthermore, compound 7g decreased the percentage of CD44+, CD133+ and ALDH+ cells. Thus, compound 7g is a promising anti-CSC agent and could serve as a candidate for the development of new anti-ovarian cancer drugs.
N-substituted acrylamide derivatives as DHODH inhibitors and preparation and use of N-substituted acrylamide derivatives
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Paragraph 0178-0179; 0182, (2019/11/04)
The invention relates to N-substituted acrylamide derivatives as DHODH inhibitors and preparation and use of the N-substituted acrylamide derivatives. In particular, the invention discloses a compoundshown in a general formula I and the preparation and use of the compound. The compound has excellent DHODH inhibitory activation, so the compound can be used for treating or preventing various diseases caused by DHODH, the various diseases include but not limited to cancer, rheumatoid arthritis, lupus erythematosus, organ transplant rejection and other autoimmune diseases, and colitis, rhinitis and other inflammatory diseases.
