7298-67-1Relevant academic research and scientific papers
Evaluation of in vitro and in vivo anticancer potential of two 5-acetamido chalcones against breast cancer
Wankhede, Sonal,Kumar, Nitesh,Simon, Lalitha,Biswas, Subhankar,Gourishetti, Karthik,Ramalingayya, Grandhi Venkata,Joshi, Mit,Rao, C. Mallikarjuna
, p. 1150 - 1163 (2017)
Two 5’acetamido chalcones, C1 and C2 were synthesized by Claisen-Schmidt condensation method and characterized by IR, LC-MS, 1H NMR and 13C NMR. These compounds were evaluated for anticancer activity in vitro in breast cancer cell lines (MCF-7 and MDA-MB-231) using MTT assay, anti-metastatic assay, apoptotic screening by AO/EB staining and in vivo in N-Methyl-N-nitrosourea (MNU) induced breast carcinoma model. Sprague-Dawley rats with developed tumors (50 mg/kg MNU i.p.) were grouped in four, namely MNU control (0.25 % of CMC p.o.), standard group (doxorubicin 2 mg/kg once in 4 days, i.p.), C1 and C2 groups (50 mg/kg p.o. each). After 21 days of treatments, tumor volume and weight were assessed. Excised tumors were subjected to DNA fragmentation study. MTT assay showed IC50 values of 62.56 and 37.8 μM by for C1 and C2. Both compounds increased apoptotic bodies more than 3 fold compared to normal control in AO/EB staining. Antimetastatic (scratch wound) assay showed a significant (p0.05) reduction in cell migration after 24 h and 48 h treatments compared to normal control. In in vivo studies, tumor weight and tumor volume were significantly (p0.05) reduced in the doxorubicin group as well as in test groups compared to MNU control. DNA fragmentation assay showed an increase in the number of bands formed in C1 and C2 compared to normal control. Results obtained from in vitro and in vivo studies demonstrated the significant anticancer potentials of C1 and C2.
Method for diacetate intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone
-
Paragraph 0022; 0026-0027; 0029-0030; 0032-0033; 0035-0036.., (2021/11/14)
The invention belongs to the field of organic photochemical and drug intermediate chemistry. The invention particularly relates to a method for synthesizing diacetate intermediate - acetamide group 5 - (-2 - 2 epoxypropoxy) acetophenone containing acetylated 3 - photochemical rearrangement reaction in series. The reactant is cooled to the polar organic solvent, Fries rearrangement is carried out directly by ultraviolet - visible light irradiation with specific wavelength, and the intermediate Fries acetyl 2 -4 - acetyl aminophenol is obtained by heating and evaporating the solvent after the reaction is finished. Sodium hydroxide was added to prepare the phenol salt. Then, an intermediate 5 - acetamide group -2 - (2, 3 - epoxypropoxy) acetophenone was obtained by reaction with epichlorohydrin. The tandem type synthesis method disclosed by the invention is simple and feasible, and low-toxicity, high-efficiency and cheap green chemical reagents are used in the synthesis process.
Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols
Chuang, Hsiang-Yu,Schupp, Manuel,Meyrelles, Ricardo,Maryasin, Boris,Maulide, Nuno
, p. 13778 - 13782 (2021/03/31)
A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.
Click chemistry synthesis, biological evaluation and docking study of some novel 2′-hydroxychalcone-triazole hybrids as potent anti-inflammatory agents
Abdu-Allah, Hajjaj H. M.,Boshra, Andrew N.,Hayallah, Alaa M.,Mohammed, Anber F.
, (2020/01/06)
A hybrid pharmacophore approach is used to design and synthesize two novel series of 2′-hydroxychalcone-triazole hybrid molecules 6a-j and 8a-j. These compounds were fully characterized by spectral and elemental analyses. They were evaluated in vitro and in vivo for anti-inflammatory activity. Most of compounds were selective inhibitors for COX-2. Among them, compounds 6d, 6f, 6i, 8c, 8e and 8h demonstrated highly potent dual inhibition of COX-2 (IC50 = 0.037–0.041 μM) and 15-LOX (IC50 = 1.41–1.80 μM). Compounds 6i, 8c and 8h showed 116%, 113% and 109% of the in vivo anti-inflammatory activity of celecoxib. Therefore, compounds 6d, 6f, 6i, 8c, 8e and 8h-j are potent dual inhibitors of COX-2 and 15-LOX. Docking study over COX-2 and 15-LOX active sites ensures the binding affinity and selectivity. These compounds are promising candidates for further development as anti-inflammatory drugs.
AHR INHIBITORS AND USES THEREOF
-
Paragraph 0362; 0363; 0366; 0367, (2019/03/02)
The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.
Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells
Abe, Takumi,Itoh, Tomoki,Terasaki, Masaru
, (2019/07/10)
A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).
Benzo heterocyclic derivatives, their preparation and their use in medicine (by machine translation)
-
Page/Page column 20; 21; 22, (2018/09/21)
The present invention relates to benzo heterocyclic derivatives, their preparation and their use in medicine. In particular, the invention relates to a general formula (I) indicated by the compound, the compound has anti-tumor of the use, the inhibition of angiogenesis and as the role of the HIF - 1 α inhibitors in the medical application. Wherein the general formula (I) of each substituent in the definition in the description of the same. (by machine translation)
Design, synthesis, and evaluation of benzofuran derivatives as novel anti-pancreatic carcinoma agents via interfering the hypoxia environment by targeting HIF-1α pathway
Xu, Xiao-li,Yang, Ying-rui,Mo, Xiao-fei,Wei, Jin-lian,Zhang, Xiao-jin,You, Qi-dong
, p. 45 - 62 (2017/05/31)
Pancreatic ductal adenocarcinoma (PDAC) is one of the most common type of pancreatic cancer, and has still been the medicinal mystery. New drugs and treatment strategies are urgently needed. In this study, 32 benzofuran derivatives are designed, synthesized and evaluated as potential agents against the pancreatic cancer. Among them, compound 9o with the best physicochemical and pharmacokinetic properties exhibited excellent cytotoxicity against many tumor cell lines. In vivo study showed that compound 9o dramatically suppressed the tumor growth of nude mice. Furthermore, compound 9o could affect the hypoxia environment through Hif-1α/VEGF pathway, resulting in the anti-angiogenic activity. These studies indicated that compound 9o was a promising candidate for the treatment of PDAC, deserving further studies.
Synthesis and evaluation of N-(benzofuran-5-yl)aromaticsulfonamide derivatives as novel HIF-1 inhibitors that possess anti-angiogenic potential
Wei, Jinlian,Yang, Yingrui,Li, Yali,Mo, Xiaofei,Guo, Xiaoke,Zhang, Xiaojin,Xu, Xiaoli,Jiang, Zhengyu,You, Qidong
, p. 1737 - 1746 (2017/03/08)
Hypoxia-inducible factor-1 (HIF-1) as a key mediator in tumor metastasis, angiogenesis, and poor patient prognosis has been recognized as an important cancer drug target. A novel series of N-(benzofuran-5-yl)aromaticsulfonamide derivatives were synthesized and evaluated as HIF-1 inhibitor. Among these compounds, 7q exhibited specific inhibitory effects on HIF-1 by downregulating the expression of HIF-1α under hypoxic conditions. It inhibited the HIF-1 transcriptional activity (IC50?=?12.5?±?0.7?μM) and secretion of VEGF (IC50?=?18.8?μM) in MCF-7 cells. Meanwhile, it also significantly suppressed hypoxia-induced migration of HUVEC cells in nontoxic concentrations. Additionally, tube formation assay demonstrated its anti-angiogenesis activity. Finally, the in vivo study indicated that compound 7q could retard angiogenesis in CAM model. These findings supported the HIF-1 inhibitory effect and anti-angiogenic potential of this class of compounds as HIF-1 inhibitor.
Synthesis and antiproliferative activity of new 1,2,3-triazole/flavone hybrid heterocycles against human cancer cell lines
Sowjanya,Jayaprakash Rao,Murthy
, p. 1864 - 1871 (2017/09/25)
A series of new 1,2,3-triazole/flavone hybrid heterocycles were synthesized from 6-amino flavone via key intermediate N-propargyl flavone 6 by adopting the Sharpless Click reaction. Copper(I) catalyzed 1,3-dipolar cycloaddition reaction that gave products in high yields. All the synthesized compounds were screened for their in vitro antiproliferative activity against four human cancer cell lines, HeLa (cervical cancer cell line), MIA PaCa (pancreatic cancer cell line), MDA-MB-231 (breast cancer cell line), and IMR 32 (neuroblastoma cancer cell line). Compounds 7a, 7b, 7d, 7g (GI50 = 0.01–0.68 μM) demonstrated promising antiproliferative activity.
