69194-89-4Relevant academic research and scientific papers
Synthesis, molecular modeling, and biological evaluation of novel 1, 3-diphenyl-2-propen-1-one based pyrazolines as anti-inflammatory agents
Bukhari, Syed Nasir Abbas,Zhang, Xin,Jantan, Ibrahim,Zhu, Hai-Liang,Amjad, Muhammad Wahab,Masand, Vijay H.
, p. 729 - 742 (2015)
A novel series of 1,3-diphenyl-2-propen-1-one (chalcone) derivatives was synthesized by a simple, eco-friendly, and efficient Claisen-Schmidt condensation reaction and used as precursors for the synthesis of new pyrazoline derivatives. All the synthesized
Synthesis, In-vitro evaluation and molecular docking studies of oxoindolin phenylhydrazine carboxamides as potent and selective inhibitors of ectonucleoside triphosphate diphosphohydrolase (NTPDase)
Afzal, Saira,al-Rashida, Mariya,Hameed, Abdul,Pelletier, Julie,Sévigny, Jean,Iqbal, Jamshed
, (2021/05/27)
Members of the ectonucleoside triphosphate diphosphohydrolases (NTPDases) constitute the major family of enzymes responsible for the maintenance of extracellular levels of nucleotides and nucleosides by catalyzing the hydrolysis of nucleoside triphosphate
Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents
Chaudhary, Bharat N.,Gandhi, Bhumi,Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Kirti V.,Patel, Kishan B.,Patel, Nirav R.,Prajapati, Navnit K.,Shah, Bhavik S.,Teli, Divya M.,Yadav, Mange Ram
, (2021/07/14)
With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.
Gold-Catalyzed Functionalization of Semicarbazides with Terminal Alkynes to Achieve Substituted Semicarbazones
Zimin, Dmitry P.,Dar'in, Dmitry V.,Eliseeva, Anastasiya A.,Novikov, Alexander S.,Rassadin, Valentin A.,Kukushkin, Vadim Yu.
supporting information, p. 6094 - 6100 (2019/08/22)
Gold-catalyzed functionalization of semicarbazides (ArNHCONHNH2) with various terminal alkynes R2C≡CH (R2 = Alk or Ar) in the presence of Ph3PAuNTf2 (3 mol-%) grants a range of substituted semicarbazo
Design, Synthesis and Antifungal Activity of Benzofuran and Its Analogues
Xu, Hang,Hou, Zhuang,Liang, Zhen,Guo, Meng-Bi,Su, Xin,Guo, Chun
, p. 1245 - 1250 (2019/11/21)
Benzofuran has antifungal activity as the inhibitor of N-myristoyltransferase. Twenty-nine novel benzofuran-semicarbazide hybrids were designed and synthesized by principle of drug combinationatory. On this basis, the benzofuran ring was simplified to a resorcinol structure, and sixteen novel 1,3-dialkoxybenzene-semicarbazide hybrids were designed and synthesized. All structures of the target compounds were characterized by HRMS and NMR. The in vitro antifungal activity of target compounds was evaluated using the microdilution broth method against eight strains of pathogenic fungi with fluconazole as positive control. According to the results of the target compounds, structure-activity relationship (SAR) is summarized. The inhibitory activity against the tested strains of simplified compounds (K01—K16) has different levels improvement compared with compounds Z01—Z29. K01—K16 showed significant antifungal activities against A. fumigatus, C. kruseii, and sensitive C. albicans 5314. Notably, compounds Z20, Z22, K10, K11 and K16 also displayed different activities against two fluconazole-resistance strains that were isolated from AIDS patients. The minimal inhibitory concentration (MIC) values against fluconazole-resistant strains were in the range of 2—8 μg/mL and 4—32μg/mL, respectively. Furthermore, molecular docking was performed to investigate the binding affinities and interaction modes between the target compound and N-myristoyltransferase.
Design, synthesis and anticancer evaluation of novel spirobenzo[h]chromene and spirochromane derivatives with dual EGFR and B-RAF inhibitory activities
Abdelatef, Shaimaa A.,El-Saadi, Mohammed T.,Amin, Noha H.,Abdelazeem, Ahmed H.,Omar, Hany A.,Abdellatif, Khaled R.A.
, p. 567 - 578 (2018/03/21)
A novel series of spirobenzo[h]chromene and spirochromane derivatives was designed, synthesized and evaluated as potential anticancer agents against MCF-7 (human breast carcinoma), HT-29 (human colorectal adenocarcinoma) and A549 (human lung carcinoma) cell lines using MTT assay. Eight compounds 7, 8e, 13a-e and 16 showed a better anticancer activity than that of sorafenib, the multi-kinase inhibitor with IC50 values between 1.78 and 5.47 μM or erlotinib with IC50 values over 20 μM. Representative compounds 8e, 13c and 16 were selected for further mechanistic investigation via EGFR, B-RAF and tubulin polymerization assays. Compound 16 was the most potent EGFR inhibitor (IC50 = 1.2 μM), yet compounds 8e, 13c and 16 displayed moderate tubulin polymerization inhibition effects. Molecular docking studies of those compounds revealed their possible binding modes into the active sites of both EGFR and B-RAF kinases. The newly developed compounds represent a therapeutically promising approach for the treatment of different types of cancer.
Design and synthesis of novel N-(4-(Pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides as potential anticonvulsant agents
Singh, Prem,Tripathi, Laxmi
, p. 2193 - 2200 (2018/09/10)
A new series of N-(4-(pyridin-2-yloxy)benzylidene)-4-[4-(substituted)phenyl]semicarbazides (PSSD1-8) were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for their possible anticonvulsant activity. All the derivatives were synthesized by the given scheme and reaction process was monitored by thin layer chromatography. The structure of synthesized derivatives was confirmed by FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The anticonvulsant activity was established after intraperitoneal administration in MES and scMET seizure models. The most active compound of the series was 1-(4-(pyridin-2-yloxy)-benzylidene)-4-p-tolylsemicarbazide (PSSD5). A molecular docking study was carried out in order to assess the interaction and binding modes with target receptor/enzyme. Titled compounds were found to strongly bind to human gamma-aminobutyric acid receptor (GABAAR-β3). A computational study was also carried to predict the pharmacokinetic properties of the synthesized compounds.
Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides
He, Zeng-Yang,Huang, Chao-Fan,Tian, Shi-Kai
supporting information, p. 4850 - 4853 (2017/09/23)
The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.
Design, synthesis and anticancer activity of dihydropyrimidinone-semicarbazone hybrids as potential human DNA ligase 1 inhibitors
Sashidhara, Koneni V.,Singh, L. Ravithej,Shameem, Mohammad,Shakya, Sarika,Kumar, Anoop,Laxman, Tulsankar Sachin,Krishna, Shagun,Siddiqi, Mohammad Imran,Bhatta, Rabi S.,Banerjee, Dibyendu
, p. 2349 - 2363 (2016/12/16)
A series of new dihydropyrimidinone-semicarbazone hybrids were successfully synthesised by integrating regioselective multicomponent reaction with the pharmacophore hybridization approach. All the synthesised compounds were evaluated for their hLig1 inhibition potency and most of them were found to be good to moderately active. Out of the tested derivatives, compound 6f showed selective anti-proliferative activity against HepG2 cells in a dose-dependent manner with an IC50 value of 10.07 ± 1.2. It also reduced cell survival at ≤20 μM concentration. Further, analysis of treated HepG2 cell lysates by western blot assay showed increased γ-H2AX levels and upregulation of p53, leading to apoptosis. In silico docking results explain the binding modes of compound 6f to the DNA-binding domain of hLig1 enzyme thereby preventing its nick sealing activity. In addition, the favourable pharmacokinetic properties suggest that this new class of hLig1 inhibitors could be promising leads for further drug development.
Synthesis of N-aryl and N-arylcarbamoylamino derivatives of 1,3-diazinane-5-carboxamide and their activity against glioblastoma LN-229 cell line
Hron, Rebecca J.,Jursic, Branko S.,Neumann, Donna M.
, p. 6183 - 6193 (2016/12/06)
Six structural motifs based on the initial (lead) structure of merbarone were designed, prepared, and tested against the glioblastoma LN-229 cell line. Three different structural moieties were modified in the search for optimal glioblastoma activity: the 1,3-diazinane moiety, the aryl moiety, and the heteroatom linker. Calculated molecular descriptors such as lipophilicity (C log P), acidic strength (calculated pKa), and polar surface area (PSA) were used to design a diverse structural library of these compounds. From six different structural motifs and 136 compounds, a handful of examples with moderate (100 μg/ml), good (10 μg/ml) and excellent (1 μg/ml) glioblastoma activity were elucidated.
