154424-13-2Relevant academic research and scientific papers
Sesquiterpene lactone-cinnamic acid derivative and salt, pharmaceutical composition and application thereof
-
Paragraph 0110-0113, (2020/08/09)
The invention provides application of sesquiterpene lactone-cinnamic acid derivatives shown as a formula (I) and salts thereof in preparation of medicines for treating cancers and auxiliary medicinesfor treating cancers.
Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study
Bai, Yajun,He, Xirui,Bai, Yujun,Sun, Ying,Zhao, Zefeng,Chen, Xufei,Li, Bin,Xie, Jing,Li, Yang,Jia, Pu,Meng, Xue,Zhao, Ye,Ding, Yanrui,Xiao, Chaoni,Wang, Shixiang,Yu, Jie,Liao, Sha,Zhang, Yajun,Zhu, Zhiling,Zhang, Qiang,Zhao, Yuhui,Qin, Fanggang,Zhang, Yi,Wei, Xiaoyang,Zeng, Min,Liang, Jing,Cuan, Ye,Shan, Guangzhi,Fan, Tai-Ping,Wu, Biao,Zheng, Xiaohui
, (2019/09/18)
Inspired by the traditional Chinese herbal pair of Polygala tenuifolia-Acori Tatarinowii for treating epilepsy, 33 novel substituted cinnamic α-asaronol esters and analogues were designed by Combination of Traditional Chinese Medicine Molecular Chemistry (CTCMMC) strategy, synthesized and tested systematically not only for anticonvulsant activity in three mouse models but also for LDH inhibitory activity. Thereinto, 68–70 and 75 displayed excellent and broad spectra of anticonvulsant activities with modest ability in preventing neuropathic pain, as well as low neurotoxicity. The protective indices of these four compounds compared favorably with stiripentol, lacosamide, carbamazepine and valproic acid. 68–70 exhibited good LDH1 and LDH5 inhibitory activities with noncompetitive inhibition type, and were more potent than stiripentol. Notably, 70, as a representative agent, was also shown as a moderately positive allosteric modulator at human α1β2γ2 GABAA receptors (EC50 46.3 ± 7.3 μM). Thus, 68–70 were promising candidates for developing into anti-epileptic drugs, especially for treatment of refractory epilepsies such as Dravet syndrome.
Synthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents
Ge, Weizhi,Hao, Xin,Han, Fangzhi,Liu, Zhongquan,Wang, Tianpeng,Wang, Mengmeng,Chen, Ning,Ding, Yahui,Chen, Yue,Zhang, Quan
, p. 445 - 469 (2019/02/12)
Triple-negative breast cancer (TNBC) is the most aggressive cancers with a high recurrence rate and rapidly acquired drug resistance among various breast cancer subtypes. There is no specific drug for treatment of TNBC. Discovery of therapeutic agents with unique modes of actions is urgently needed. In this study, a series of seventy parthenolide derivatives was designed, synthesized, and evaluated for their anti-TNBC activities. Compound 7d exhibited the most potent activity against different breast cancer cells with IC50 values ranging from 0.20 μM to 0.27 μM, which demonstrated 11.6- to 18.6-fold improvement comparing to that of the parent compound parthenolide with IC50 values of 2.68–4.63 μM. It is worth to note that 7d was more active than the positive control drug ADR. Moreover, compound 7d could induce apoptosis of SUM-159 cells through mitochondria pathway and cause G1 phase arrest of SUM-159 cells. These findings indicate that compound 7d deserves further studies as a lead compound for ultimate discovery of effective anti-TNBC drug.
Substrate-Dependent Mechanistic Divergence in Decarboxylative Heck Reaction at Room Temperature
Hossian, Asik,Bhunia, Samir Kumar,Jana, Ranjan
, p. 2521 - 2533 (2016/04/01)
We report herein a Pd(II)-catalyzed Heck-type coupling between arene carboxylic acids and alkenes at room temperature. Mechanistically, the reaction proceeds in two distinct pathways where electron-rich substrates undergo a palladium(II)-catalyzed decarboxylation and electron-deficient substrates proceed through silver(I)-assisted decarboxylation. Dimethyl sulfoxide (DMSO) or sulfide ligands have positive and negative roles in the reaction outcome, respectively. The present protocol is combined for the peptide modification under mild reaction conditions.
Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6
Yamaguchi, Yuki,Akimoto, Ichie,Motegi, Kyoko,Yoshimura, Teruki,Wada, Keiji,Nishizono, Naozumi,Oda, Kazuaki
, p. 997 - 1001 (2013/11/19)
Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.
Pd-catalyzed decarboxylative arylation of silyl enol ester sp3 β-C-H bond under aerobic conditions
Fu, Zhengjiang,Huang, Shijun,Kan, Jian,Su, Weiping,Hong, Maochun
supporting information; experimental part, p. 11317 - 11321 (2011/02/16)
Pd-catalyzed aerobic oxidative coupling of various benzoic acids with silyl enol esters proceeds via a combination of decarboxylation with sp3 β-C-H bond activation to give Heck-type products. Mechanistic studies reveal this coupling involves in situ generation of olefin from aerobic oxidation of silyl enolate, followed by decarboxylative Heck coupling.
Pd-catalyzed dearboxylative heck coupling with dioxygen as the terminal oxidant
Fu, Zhengjiang,Huang, Shijun,Su, Weiping,Hong, Maochun
supporting information; experimental part, p. 4992 - 4995 (2010/12/25)
Pd-catalyzed decarboxylative Heck coupling of aromatic carboxylic acids with various olefins is developed using O2 as the terminal oxidant. Enhancement of O2 pressure leads to improving reaction turnover in this transformation and allows significantly reducing catalyst loading for efficient conversion of electron-rich benzoic acids. A Pd catalyst supported by a carbene ligand enables using electron-deficient benzoic acids as coupling partners.
Sodium 2-(2-pyridin-3-ylethylamino)sulfonate: an efficient ligand and base for palladium-catalyzed Heck reaction in aqueous media
Pawar, Shivaji S.,Dekhane, Deepak V.,Shingare, Murlidhar S.,Thore, Shivaji N.
, p. 4252 - 4255 (2008/09/21)
The first successful Pd(OAc)2, N-donor ligand and base mediated Heck coupling reaction of aryl halides and alkenes in water is described. The corresponding Heck products were obtained in good to excellent yields.
1-(2-Iodophenyl)-1H-tetrazole as a ligand for Pd(II) catalyzed Heck reaction
Gupta, Arun Kumar,Song, Chung Hyun,Oh, Chang Ho
, p. 4113 - 4116 (2007/10/03)
1-(2-Iodophenyl)-1H-tetrazole 2 was synthesized by the reaction of 2-iodoaniline, sodium azide and triethyl orthoformate in acetic acid. The newly synthesized ligand 2 was successfully used in Heck reaction to give the cross-coupled products in excellent yields.
Occurrence of 2,6-dimethoxy cinnamaldehyde in Taxus floridana and structural revision of taxiflorine to taxchinin M
Rao, Koppaka V.,Johnson, James H.
, p. 1361 - 1364 (2007/10/03)
Taxiflorine, originally isolated from the needles of Taxus floridana and described previously, has its structure revised to that of taxchinin M. Four other known taxanes also isolated were: 1-deoxy baccatin IV, 1-hydroxy baccatin 1, 10-deacetyl paclitaxel
