64244-30-0Relevant articles and documents
Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway
Shang, Fan-Fan,Wang, Jing Ying,Xu, Qian,Deng, Hao,Guo, Hong-Yan,Jin, Xuejun,Li, Xiaoting,Shen, Qing-Kun,Quan, Zhe-Shan
, (2021/05/03)
Four series of hypoxia-inducible factor-1 alpha (HIF-1α) functioning derivatives stemming from modifications to the C-29 carboxyl group of celastrol were designed and synthesized, and their anticancer activities were evaluated. To address the structure and activity relationship of each derivative, extensive structural changes were made. HRE luciferase reporter assay demonstrated that 12 modified compounds showed superior HIF-1α inhibitory activity. Among them, compound C6 exhibited the best features: firstly, the strongest HIF-1α inhibitory activity (IC50 = 0.05 μM, 5-fold higher than that of celastrol); secondly, lower cytotoxicity (22-fold lower, C6-16.85 μM vs celastrol-0.76 μM). Thus, the safety factor of C6 was about 112 times higher than that of celastrol. Western blot assay indicated that C6 may inhibit the expression of HIF-1α protein in cells. Additionally, C6 hindered tumor cell cloning, migration and induced cell apoptosis. It is worth mentioning that in the mouse tumor xenograft model, C6 (10 mg/kg) displayed good antitumor activity in vivo, showing a better inhibition rate (74.03%) than the reference compound 5-fluorouracil (inhibition rate, 59.58%). However, the celastrol treatment group experienced collective death after four doses of the drug. Moreover, C6 minimally affected the mouse weight, indicating that its application in vivo has little toxic effect. H&E staining experiments show that it could also exacerbate the degree of tumor cell damage. The results of water solubility experiment show that the solubility of C6 is increased by 1.36 times than that of celastrol. In conclusion, C6 is a promising antitumor agent through HIF-1α pathway.
Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents
Lan, Xianmin,Xie, Dandan,Yin, Limin,Wang, Zhenzhen,Chen, Jin,Zhang, Awei,Song, Baoan,Hu, Deyu
, p. 4270 - 4273 (2017/09/12)
Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67 μg/mL and 216.30 μg/mL, which were obviously superior to that of Ningnanmycin (352.08 μg/mL and 262.53 μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.
Novel coumarin-containing aminophosphonatesas antitumor agent: synthesis, cytotoxicity, DNA-Binding and apoptosis evaluation
Li, Ya-Jun,Wang, Cai-Yi,Ye, Man-Yi,Yao, Gui-Yang,Wang, Heng-Shan
, p. 14791 - 14809 (2015/09/21)
A series of novel coumarin-containing α-aminophosphonates were synthesized and evaluated for their antitumor activities against Human colorectal (HCT-116), human nasopharyngeal carcinoma (human KB) and human lung adenocarcinoma (MGC-803) cell lines in vit
Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates
Yao, Gui-Yang,Ye, Man-Yi,Huang, Ri-Zhen,Li, Ya-Jun,Pan, Ying-Ming,Xu, Qing,Liao, Zhi-Xin,Wang, Heng-Shan
supporting information, p. 501 - 507 (2014/01/23)
Several rhein α-aminophosphonates conjugates (5a-5q) were synthesized and evaluated for in vitro cytotoxicity against HepG-2, CNE, Spca-2, Hela and Hct-116 cell lines. Some compounds showed relatively high cytotoxicity. Especially, compound 5i exhibited t
Coumarin-containing aminophosphonates bridged with chiral side chain: Synthesis and influence of chirality on cytotoxicity and DNA binding
Li, Ya-Jun,Ye, Man-Yi,Huang, Ri-Zhen,Yao, Gui-Yang,Pan, Ying-Ming,Liao, Zhi-Xin,Wang, Heng-Shan
, p. 3144 - 3156 (2014/05/06)
A series of novel coumarin-containing α-Aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2- bromophenyl)methylphosphonate) was
Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives
Huang, Xiao-Chao,Wang, Meng,Pan, Ying-Ming,Tian, Xiao-Yan,Wang, Heng-Shan,Zhang, Ye
, p. 5283 - 5289 (2013/09/23)
A series of novel α-aminophosphonate derivatives containing DHA structure were designed and synthesized as antitumor agents. In vitro antitumor activities of these compounds against the NCI-H460 (human lung cancer cell), A549 (human lung adenocarcinoma ce
Synthesis and bioactivities of α-aminophosphonate derivatives containing benzothiazole and thiourea moieties
Liu, Jing-Zi,Song, Bao-An,Bhadury, Pinaki S.,Hu, De-Yu,Yang, Song
, p. 61 - 70 (2012/04/10)
The synthesis of a series of novel α-aminophosphonate derivatives containing benzothiazole and thiourea moieties from substituted 2-aminobenzothiazoles and synthetic intermediates O,O'-dialkylisothiocyanat- (phenyl)methylphosphonates under microwave irradiation has been demonstrated. Several salient features, such as good to excellent yields, shorter reaction times, milder reaction conditions, and simple purification procedures, make the present synthetic protocol highly attractive to access the title compounds. Bioassays indicated that most of the compounds possessed broad-spectrum insecticidal and antiviral activities against Tobacco Mosaic Virus (TMV) in vivo. Interestingly, in comparison with control insecticide Avermectin, two compounds displayed remarkably high in vitro insecticidal activities against Plutella xylostella. Furthermore, according to the results from preliminary bioassay, all were associated with moderate to good anti-TMV activities. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Tables S1-S4. Figures S1-S52.] Copyright Taylor and Francis Group, LLC.
Synthesis and antiviral activity of novel pyrazole amides containing α-aminophosphonate moiety
Wu, Lintao,Song, Baoan,Bhadury, Pinaki S.,Yang, Song,Hu, Deyu,Jin, Linhong
scheme or table, p. 389 - 396 (2011/06/20)
A series of novel pyrazole amides J1-J15 containing an α-aminophosphonate moiety were synthesized and subsequently characterized by spectral (IR, 1H-, 13C-, 31P-, and 19F-NMR) data and elemental analysis. The racemic sample of J1 was further separated into its enantiomers under normal-phase condition on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The synthesized compounds revealed certain degree of antiviral activity in the bioassay. The title compounds (J 3, J10, and J12) showed some curative activities (39.9%, 41.8%, 50.1%, respectively) against tobacco mosaic virus at 0.5 mg/mL.
Synthesis and biological evaluation of novel phosphonates derivatives of as potential antitumor agents
Jin, Chuanfei,Liang, Yong-Ju,He, Hongwu,Fu, Liwu
experimental part, p. 2096 - 2103 (2011/12/01)
A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR, 31P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU. Copyright Taylor & Francis Group, LLC.
Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety
Yang, Xuan,Song, Baoan,Jin, Linhong,Wei, Xue,Bhadury, S. Pinaki,Li, Xiangyang,Yang, Song,Hu, Deyu
scheme or table, p. 103 - 109 (2011/12/21)
Starting from 1-((1R,2R)-2-aminocyclohexyl)-3-substituted thioureas (3a-c) and substituted isothiocyanates (9a-d), chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a-l were prepared and completely characterized by elemental analysis, physical and spectral (IR, 1H NMR, 13C NMR, 31P NMR) data. The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus (CMV) at 0.5 mg/mL in vivo (inhibitory rate = 60.3%, 64.8% respectively) and tobacco mosaic virus (TMV) at 0.5 mg/mL in vivo (inhibitory rate = 50.3%, 50.8% respectively), which were comparable to the values shown by standard reference (58.7%) and commercial product Ningnanmycin (56.3%), respectively. Chiral compound 10e displayed more potent antiviral activity (EC50 = 0.149 mg/mL) than Ningnanmycin (EC50 = 0.201mg/mL) against CMV.
