480-66-0Relevant articles and documents
Synthesis, photoluminescence and biological properties of terbium(III) complexes with hydroxyketone and nitrogen containing heterocyclic ligands
Poonam,Kumar, Rajesh,Boora, Priti,Khatkar, Anurag,Khatkar,Taxak
, p. 304 - 310 (2016)
The ternary terbium(III) complexes [Tb(HDAP)3·biq], [Tb(HDAP)3·dmph] and [Tb(HDAP)3·bathophen] were prepared by using methoxy substituted hydroxyketone ligand HDAP (2-hydroxy-4,6-dimethoxyacetophenone) and an ancillary ligand 2,2-biquinoline or 5,6-dimethyl-1,10-phenanthroline or bathophenanthroline respectively. The ligand and synthesized complexes were characterised based on elemental analysis, FT-IR and 1H NMR. Thermal behaviour of the synthesized complexes illustrates the general decomposition patterns of the complexes by thermogravimetric analysis. Photophysical properties such as excitation spectra, emission spectra and luminescence decay curves of the complexes were investigated in detail. The main green emitting peak at 548 nm can be attributed to 5D4 → 7F5 of Tb3+ ion. Thus, these complexes might be used to make a bright green light-emitting diode for display purpose. In addition the in vitro antibacterial activities of HDAP and its Tb(III) complexes against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and antifungal activities against Candida albicans and Aspergillus niger are reported. The Tb3+ complexes were found to be more potent antimicrobial agent as compared to the ligand. Among all these complexes, [Tb(HDAP)3·bathophen] exhibited excellent antimicrobial activity which proves its potential usefulness as an antimicrobial agent. Furthermore, in vitro antioxidant activity tests were carried out by using DPPH method which indicates that the complexes have considerable antioxidant activity when compared with the standard ascorbic acid.
Biomimetic total synthesis and structure confirmation of myrtucommulone K
Zhou, Wen-Li,Tan, Hai-Bo,Qiu, Sheng-Xiang,Chen, Guang-Ying,Liu, Hong-Xin,Zheng, Chao
, p. 1817 - 1821 (2017)
A confirmed structure of meroterpenoid myrtucommulone K, which is vastly different from the originally reported one, is conducted. The first biomimetic total synthesis towards the assignment of its absolute configuration has been efficiently accessed in 5 steps, and key to the success was a heteroatom Diels-Alder cycloaddition. The structure of myrtucommulone K was re-elucidated and confirmed by extensive spectroscopic interpretation of 1D and 2D NMR.
Frutescone A-G, Tasmanone-Based Meroterpenoids from the aerial parts of Baeckea frutescens
Hou, Ji-Qin,Guo, Cui,Zhao, Jian-Juan,He, Qi-Wei,Zhang, Bao-Bao,Wang, Hao
, p. 1448 - 1457 (2017)
Frutescone A-G [(1-6), (+)-7, (-)-7], a new group of naturally occurring tasmanone-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens L. Compounds 1 and 4 featured a rare carbon skeleton with an unprecedented oxa-spiro[5.8] tetradecadiene ring system, existing as two favored equilibrating conformers in CDCl3 solution, identified by variable-temperature NMR. The regioselective syntheses of 4-7 were achieved in a concise manner by a biomimetically inspired key hetero-Diels-Alder reaction "on water". Compounds 1, 4, and 5 exhibited moderate cytotoxicities in vitro.
Isolation and biomimetic synthesis of (±)-calliviminones A and B, two novel Diels-Alder adducts, from Callistemon viminalis
Wu, Lin,Luo, Jun,Zhang, Yalong,Zhu, Mengdi,Wang, Xiaobing,Luo, Jianguang,Yang, Minghua,Yu, Boyang,Yao, Hequan,Dai, Yue,Guo, Qinglong,Chen, Yijun,Sun, Hongbin,Kong, Lingyi
, p. 229 - 232 (2014)
(±)-Calliviminones A (1) and B (2), two Diels-Alder adducts of polymethylated phloroglucinol and myrcene with unprecedented spiro-[5.5] undecene skeleton, were isolated from the fruits of Callistemon viminalis. Structural elucidation was accomplished by NMR spectra studies, and the biomimetic synthesis of compounds 1 and 2 confirmed the pivotal role of Diels-Alder reaction in the plausible biosynthetic pathway. Compounds 1 and 2 were also the first example of Carbon Diels-Alder adducts between phloroglucinol and terpene. Bioactivity scan indicated that 1 and 2 showed moderate inhibition on NO production on lipopolysaccharide-induced RAW264.7 macrophages.
Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate
Qin, Xu-Jie,Rauwolf, Tyler J.,Li, Pan-Pan,Liu, Hui,McNeely, James,Hua, Yan,Liu, Hai-Yang,Porco, John A.
, p. 4291 - 4296 (2019)
Rhodomyrtusials A–C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syntheses of six isolates were achieved in six steps utilizing a reactive enetrione intermediate generated in situ from a readily available hydroxy-endoperoxide precursor.
Identification of novel androgen receptor degrading agents to treat advanced prostate cancer
Wu, Hongxi,Ren, Jie,Zhao, Lulu,Li, Zhiyu,Ye, Wanli,Yang, Yong,Wang, Jubo,Bian, Jinlei
, (2021/03/24)
Prostate cancer (PCa) is one of the most common malignancies affecting men worldwide. Androgen receptor (AR) has been a target of PCa treatment for nearly six decades. AR antagonists/degraders can effectively treat PCa caused by increased AR overexpression. However, all approved AR antagonists have similar chemical structures and exhibit the same mode of action on the protein. Although initially effective, resistance to these AR antagonists usually develops. Therefore, this calls for the identification of novel chemical structures of AR antagonists to overcome the resistance. Herein, we employed the synergetic combination of virtual and experimental screening to identify a flavonoid compound which not only effectively inhibits AR transcriptional activity, but also induces the degradation of the protein. Based on this compound, we designed and synthesized a series of derivatives. We discovered that the most potent compound 10e could effectively inhibit AR transcriptional activity, and possessed a profound ability to cause degradation of both full length- and ARv7 truncated forms of human AR. Notably, 10e efficiently inhibited the growth of ARv7 dependent prostate cancer cell-lines, which are completely resistant to all current anti-androgens. Compound 10e also showed strong antitumor activity in the LNCaP (androgen dependent prostate cancer cell line) in vivo xenograft model. These results provide a foundation for the development of a new class of AR antagonists.
The first synthesis of podocarflavone A and its analogs and evaluation of their antimycobacterial potential against Mycobacterium tuberculosis with the support of virtual screening
Puranik, Ninad V.,Swami, Sagar,Misar, Ashwini V.,Mamgain, Ritu,Gulawani, Swapnaja S.,Sarkar, Dhiman,Srivastava, Pratibha,Srivastava, Pratibha
supporting information, (2021/03/15)
The first synthetic route developed for Podocarflavone A reported from Podocarpus macrophyllus and its analogs in 7 steps. Computational analysis for binding with the pantothenate kinase (3AVO) of Mycobacterium tuberculosis showed their docking score (ds) in the range of ?8.9 to ?9.3 Kcal/mol. MD simulations delineated the stability of the protein-ligand complexes in the TIP3P model. MMGBSA and MMPBSA values of 8d were ?42.46 Kcal/mol and ?14.58 Kcal/mol, respectively. Further in-vitro antitubercular screening of compounds 8a, 8d, and 8e against M. tuberculosis H37Ra using XRMA protocol exhibited promising antimycobacterial activity with IC50 values 21.82μg/mL, 15.55 μg/mL, and 16.56 μg/mL, respectively. Compounds 8a, 8d, and 8e showed antibacterial activity with IC50 values 41.56 μg/mL, 24.72 μg/mL, and 72.45 μg/mL respectively against the Staphylococcus aureus. 8a and 8d showed inhibition with IC50 values 39.6 μg/mL and 27.64 μg/mL, respectively, against Bacillus subtilis. The present study could help in the further development of lead molecules against tuberculosis.
Application of myrtle ketone compound in preparation of novel coronavirus SARS-CoV-2 medicine
-
Paragraph 0045; 0048-0050, (2021/12/07)
The invention discloses application of myrtle ketone compounds in preparation of novel coronavirus SARS-CoV-2 medicaments. The myrtle ketone compound has obvious inhibition effect on novel coronavirus SARS-CoV-2. Mechanisms include, but are not limited to, inhibition of new coronavirus SARS-CoV-2 into cells, preventing the replication of new coronavirus SARS-CoV-2 in the host cell, and timely modulating apoptosis of infected cells. To the myrtle ketone compound provided by the invention, the novel coronavirus SARS-CoV-2 has a remarkable inhibiting effect, and the cytotoxicity is relatively small. It can therefore be used for the prophylaxis or treatment of neoplastic pneumonitis. The invention is expected to provide new candidate drug molecules for clinic treatment of nebrodensis.
Peachy ketones and their application in the preparation of anti-flu virus drugs
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Paragraph 0049-0054, (2021/12/07)
The present invention discloses myrtle ketone compounds and their applications in the preparation of anti-influenza virus drugs. The myrtle ketone compounds of the present invention have a significant inhibitory effect on influenza viruses, the mechanism of action of which includes (but is not limited to) inhibiting influenza viruses entering cells, preventing the replication of influenza viruses in host cells, and timely regulating the apoptosis program of infected cells. The myrtle ketone compounds provided by the present invention have inhibitory effects on both influenza A and B viruses, the activity is better than the positive drug ribavirin (Ribavrin), and therefore can be used to prevent or treat influenza. The present invention is expected to provide a new active lead compound or drug candidate molecule for the clinical treatment of influenza.
Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones
Hu, Caijuan,Li, Guoxun,Mu, Yu,Wu, Wenxi,Cao, Bixuan,Wang, Zixuan,Yu, Hainan,Guan, Peipei,Han, Li,Li, Liya,Huang, Xueshi
supporting information, p. 6008 - 6020 (2021/05/06)
Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.
