22367-82-4Relevant academic research and scientific papers
Benzofuran-Based Carboxylic Acids as Carbonic Anhydrase Inhibitors and Antiproliferative Agents against Breast Cancer
Abdel-Aziz, Hatem A.,Al-Sanea, Mohammad M.,Al-Warhi, Tarfah,Aljaeed, Nada,Alotaibi, Ohoud J.,Eldehna, Wagdy M.,Elsayed, Zainab M.,Nocentini, Alessio,Supuran, Claudiu T.
, p. 1022 - 1027 (2020)
Pursuing our effort for developing effective inhibitors of the cancer-related hCA IX isoform, here we describe the synthesis of novel benzofuran-based carboxylic acid derivatives, featuring the benzoic (9a-f) or hippuric (11a,b) acid moieties linked to 2-
Quantum reality in the selective reduction of a benzofuran system
Coaviche-Yoval, Arturo,Andrade-Jorge, Erik,Pérez-González, Cuauhtémoc,Luna, Héctor,Tovar-Miranda, Ricardo,Trujillo-Ferrara, José G.
, (2019)
Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson's hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ωk) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (Pk+) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction.
Development of novel benzofuran-based SLC-0111 analogs as selective cancer-associated carbonic anhydrase isoform IX inhibitors
Shaldam, Moataz,Eldehna, Wagdy M.,Nocentini, Alessio,Elsayed, Zainab M.,Ibrahim, Tamer M.,Salem, Rofaida,El-Domany, Ramadan A.,Capasso, Clemente,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, (2021)
In the present study, we describe the design of different series of benzofuran-based derivatives as potential carbonic anhydrase inhibitors (CAIs). The adopted design is based on bioisosteric replacement for the p-fluorophenyl SLC-0111 tail with the lipop
Synthesis, SAR, molecular docking and antituberculosis study of 3-methyl-1-benzofuran-2-carbohydrazide
Thorat, Bapu R.,Nazirkar, Bhusan,Thorat, Vaishali B.,More, Kishor,Jagtap, Ravindra,Yamgar, Ramesh
, p. 2346 - 2352 (2016)
3-Methyl-1-benzofuran-2-carbohydrazide was synthesized from 2-hydroxy acetophenone. To deduce the antibacterial and anticancer activity of the 3-methyl-1-benzofuran-2-carbohydrazide, it is docked with different biomarkers of cancer cell and bacteria. The
Development of novel benzofuran-isatin conjugates as potential antiproliferative agents with apoptosis inducing mechanism in Colon cancer
Eldehna, Wagdy M.,Salem, Rofaida,Elsayed, Zainab M.,Al-Warhi, Tarfah,Knany, Hamada R.,Ayyad, Rezk R.,Traiki, Thamer Bin,Abdulla, Maha-Hamadien,Ahmad, Rehan,Abdel-Aziz, Hatem A.,El-Haggar, Radwan
, p. 1424 - 1435 (2021/07/02)
In the current work, a new set of carbohydrazide linked benzofuran-isatin conjugates (5a–e and 7a–i) was designed and synthesised. The anticancer activity for compounds (5b–d, 7a, 7b, 7d and 7g) was measured against NCI-55 human cancer cell lines. Compound 5d was the most efficient, and thus subjected to the five-dose screen where it showed excellent broad activity against almost all tested cancer subpanels. Furthermore, all conjugates (5a–e and 7a–i) showed a good anti-proliferative activity towards colorectal cancer SW-620 and HT-29 cell lines, with an excellent inhibitory effect for compounds 5a and 5d (IC50 = 8.7 and 9.4 μM (5a), and 6.5 and 9.8 μM for (5d), respectively). Both compounds displayed selective cytotoxicity with good safety profile. In addition, both compounds provoked apoptosis in a dose dependent manner in SW-620 cells. Also, they significantly inhibited the anti-apoptotic Bcl2 protein expression and increased the cleaved PARP level that resulted in SW-620 cells apoptosis.
Discovery of a promising agent IQZ23 for the treatment of obesity and related metabolic disorders
Chen, Shuo-Bin,Hu, Yu-Tao,Huang, Shi-Liang,Huang, Zhi-Shu,Li, Chan,Li, Qing-Jiang,Ou, Tian-Miao,Rao, Yong,Song, Bing-Bing,Song, Qin-Qin,Tan, Jia-Heng,Wang, Hong-Gen,Xu, Yao-Hao,Xu, Zhao,Ye, Ji-Ming,Yu, Hong,Zhong, Guo-Ping
, (2020/03/11)
Discovery of novel anti-obesity agents is a challenging and promising research area. Based on our previous works, we synthesized 40 novel β-indoloquinazoline analogues by altering the skeleton and introducing preferential side chains, evaluated their lipid-lowering activity and summarized the structure-activity relationships. In combination with an evaluation of the lipid-lowering efficacies, AMP-dependent activated protein kinase (AMPK) activating ability and liver microsomal stability, compound 23 (named as IQZ23) was selected for further studies. IQZ23 exerted a high efficacy in decreasing the triglyceride level (EC50 = 0.033 μM) in 3T3-L1 adipocytes. Mechanistic studies revealed the lipid-lowering activity of IQZ23 was dependent on the AMPK pathway by modulating ATP synthase activity. This activation was accompanied by mitochondrial biogenesis and oxidation capacity increased, and insulin sensitivity enhanced in pertinent cell models by various interventions. Correspondingly, IQZ23 (20 mg/kg, i.p.) treatment significantly reversed high fat and cholesterol diet (HFC)- induced body weight increases and accompanying clinical symptoms of obesity in mice but without indicative toxicity. These results indicate that IQZ23 could be a useful candidate for the treatment of obesity and related metabolic disorders.
4-Hydroxy-3-methylbenzofuran-2-carbohydrazones as novel LSD1 inhibitors
Gao, Yuan,He, Xingrui,Hui, Zi,Shen, Guodong,Wang, Shuo,Xie, Tian,Ye, Xiang-Yang
, (2020/03/31)
Histone lysine specific demethylase 1 (LSD1 or KDM1A) is a potential therapeutic target in oncology due to its overexpression in various human tumors. We report herein a new class of benzofuran acylhydrazones as potent LSD1 inhibitors. Among the 31 compounds prepared, 14 compounds exhibited excellent LSD1 inhibitory activity with IC50 values ranging from 7.2 to 68.8 nM. In cellular assays, several compounds inhibited the proliferations of various cancer cell lines, including PC-3, MCG-803, U87 MG, PANC-1, HT-29 and MCF-7. This opens up the opportunity for further optimization and investigation of this class compounds for potential cancer treatment.
Discovery and Development of a Series of Pyrazolo[3,4- d]pyridazinone Compounds as the Novel Covalent Fibroblast Growth Factor Receptor Inhibitors by the Rational Drug Design
Wang, Yulan,Dai, Yang,Wu, Xiaowei,Li, Fei,Liu, Bo,Li, Chunpu,Liu, Qiufeng,Zhou, Yuanyang,Wang, Bao,Zhu, Mingrui,Cui, Rongrong,Tan, Xiaoqin,Xiong, Zhaoping,Liu, Jia,Tan, Minjia,Xu, Yechun,Geng, Meiyu,Jiang, Hualiang,Liu, Hong,Ai, Jing,Zheng, Mingyue
, p. 7473 - 7488 (2019/09/03)
Alterations of fibroblast growth factor receptors (FGFRs) play key roles in numerous cancer progression and development, which makes FGFRs attractive targets in the cancer therapy. In the present study, based on a newly devised FGFR target-specific scorin
Synthesis and biological evaluation of novel 2,3-disubstituted benzofuran analogues of GABA as neurotropic agents
Coaviche-Yoval, Arturo,Luna, Héctor,Soriano-Ursúa, Marvin A.,Tovar-Miranda, Ricardo,Trujillo-Ferrara, José G.
, p. 77 - 86 (2019/07/12)
Background: Benzofurans are heterocyclic compounds with neurotropic activity. Some have been developed for the treatment of acute and degenerative neuronal injuries. Objective: The study aimed to evaluate the in silico binding of some promising benzofurans on the GABA receptors, and the in vivo neurotropic activity of benzofuran analogues (BZF 6-10) of gamma-aminobutyric acid (GABA) on a seizure model. Methods: The ligands with the best physicochemical attributes were docked on two GABA receptors (the alpha-1 subunit of GABAA-R and GBR1 subunit of GABAB-R). Selected benzofuran derivatives were synthesized by a multistep procedure and characterized. To examine the neurotropic effects, mice were pretreated with different concentrations of the compounds prior to PTZ- or 4- AP-induced seizures. We assessed acute toxicity, motor behavior, and the effects on seizures. Results: The tested ligands that complied with Lipinski’s rule of five were tested in silico with GABAA-R (δG = -5.51 to -5.84 kcal/mol) at the allosteric site for benzodiazepines. They bound to a similar cluster of residues as the reference compound (gaboxadol, δG = -5.51 kcal/mol). Synthesis was achieved with good overall yields (42-9.7percent). Two compounds were selected for biological tests (BZF-7 and rac-BZF-10) on a mouse model of seizures, induced by pentylenetetrazol (PTZ) or 4-aminopyridine (4-AP). PTZ-induced seizures are associated with GABA receptors, and those 4-AP-induced with the blockage of the delayed rectifier-type potassium channel, which promotes the release of the NMDA-sensitive glutamatergic ionotropic receptor and other neurotransmitters. The biological assays demonstrated that BZF-7 and rac-BZF-10 do not protect against seizures. Indeed, BZF-7 increased the number of PTZ-induced seizures and decreased latency time. The 4-AP model apparently showed a potentiation of seizure effects after administration of the BZF-analogues, evidenced by the incidence and severity of the seizures and reduced latency time. Conclusion: The results suggest that the test compounds are GABAergic antagonists with stimulatory activity on the CNS.
New One-Pot Synthesis of Polysubstituted Benzofurans and Benzo-1,4-dioxines
Sakhabutdinova,Raskil’dina,Zlotskii,Sultanova
, p. 233 - 236 (2018/11/21)
It has been revealed that the copper(II) triflate catalyzed reaction of ethyl-2-diazo-3-oxobutanoate with phenols followed by cyclization of the intermediate enol in the presence of polyphosphoric acid is a simple and efficient method of synthesis of polysubstituted benzofurans. The use of pyrocatechol leads to the corresponding substituted 1,4-benzodioxine-2-carboxylates as major products.
