2028-74-2Relevant academic research and scientific papers
Design, synthesis, molecular docking and biological screening of N-ethyl-N-methylbenzenesulfonamide derivatives as effective antimicrobial and antiproliferative agents
Abd El-Gilil, Shimaa M.
, p. 144 - 156 (2019)
Sulfonamides are the most famous agents, which have been utilized for preparation of effective antiproliferated agents. Therefore, this article describes the synthesis of new series of N-ethyl-N-methylbenzenesulfonamide derivatives having various biologically active moieties such as, thiazoles 3, 4, 11, 12, 14, 15, 21, 1,3,4-thiadiazine 6, imidazo[2,1-b]thiazole 8, 2-oxo-2H-chromene 17, and 3-oxo-3H-benzo[f]chromene 19, starting with 4-(2-bromoacetyl)-N-ethyl-N-methylbenzenesulfonamide (2), that was synthesized from the interaction of 4-acetyl-N-ethyl-N-methylbenzenesulfonamide (1) with bromine under stirring in dioxane/diethylether mixture. The newly structures were be proved via their elemental analysis and spectral data. However, they were also screened for their cytotoxic activity against two different human cell lines, alveolar adenocarcinoma carcinoma (lung) (A-549) and liver carcinoma (HepG2) and antimicrobial. Compound 8 having imidazo[2,1-b]thiazole moiety exhibited the most potent cytotoxic activity against (A-549) cell line (SI; 30.77). While, compound 11 having 2-cyanomethyl thiazole moiety showed significant cytotoxic activity against (HepG2) cell line (SI; 67.11). On the other hand, compound 9 having 4-chlorophenyl moiety exerted significant antimicrobial activity more than the reference drugs. Molecular Operating Environment (MOE) was performed for the synthesized compounds to study their mode of action as inhibitors against DHFR enzyme active sites.
8-Substituted 1,3-dimethyltetrahydropyrazino[2,1-f]purinediones: Water-soluble adenosine receptor antagonists and monoamine oxidase B inhibitors
Brunschweiger, Andreas,Koch, Pierre,Schlenk, Miriam,Rafehi, Muhammad,Radjainia, Hamid,Küppers, Petra,Hinz, Sonja,Pineda, Felipe,Wiese, Michael,Hockemeyer, J?rg,Heer, Jag,Denonne, Frédéric,Müller, Christa E.
, p. 5462 - 5480 (2016)
Multitarget approaches, i.e., addressing two or more targets simultaneously with a therapeutic agent, are hypothesized to offer additive therapeutic benefit for the treatment of neurodegenerative diseases. Validated targets for the treatment of Parkinson's disease are, among others, the A2Aadenosine receptor (AR) and the enzyme monoamine oxidase B (MAO-B). Additional blockade of brain A1ARs may also be beneficial. We recently described 8-benzyl-substituted tetrahydropyrazino[2,1-f]purinediones as a new lead structure for the development of such multi-target drugs. We have now designed a new series of tetrahydropyrazino[2,1-f]purinediones to extensively explore their structure–activity-relationships. Several compounds blocked human and rat A1and A2AARs at similar concentrations representing dual A1/A2Aantagonists with high selectivity versus the other AR subtypes. Among the best dual A1/A2AAR antagonists were 8-(3-(4-chlorophenyl)propyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione (41, Kihuman A1: 65.5?nM, A2A: 230?nM; Kirat A1: 352?nM, A2A: 316?nM) and 1,3-dimethyl-8-((2-(thiophen-2-yl)thiazol-4-yl)methyl)-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione (57, Kihuman A1: 642?nM, A2A: 203?nM; Kirat A1: 166?nM, A2A: 121?nM). Compound 57 was found to be well water-soluble (0.7?mg/mL) at a physiological pH value of 7.4. One of the new compounds showed triple-target inhibition: (R)-1,3-dimethyl-8-(2,1,3,4-tetrahydronaphthalen-1-yl)-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione (49) was about equipotent at A1and A2AARs and at MAO-B (Kihuman A1: 393?nM, human A2A: 595?nM, IC50human MAO-B: 210?nM) thus allowing future in vivo explorations of the intended multi-target approach.
Acetylacetaldehyde Dimethyl Acetal as Versatile Precursors for the Synthesis of Arylazonicotinic Acid Derivatives: Green Multicomponent Syntheses of Bioactive Poly-Heteroaromatic Compounds
Hassaneen, Huwaida M. E.,Abdelhamid, Ismail A.
, p. 1048 - 1053 (2017)
A simple and efficient one-pot synthesis of interesting arylhydrazonals could be achieved via coupling of acetylacetaldehyde dimethyl acetal with aromatic diazonium salts. Dimroth type rearrangement was observed during the reaction of the arylhydrazonals with malononitrile or ethyl cyanoacetate leading to the formation of arylazonicotinic acid derivatives. The reaction of arylhydrazonals with malononitrile and aldehydes in the presence of DABCO afforded 4-styryl-1,2-dihydropyridine-3-carbonitrile whose structure was established by X-ray crystallography. Pyrazolyl-enaminone was accomplished and used as a scaffold to synthesize bioactive fused heterocyclic compounds such as 1,2,4-triazolo[1,5-a]pyrimidine 28, benzo[4,5]imidazo[1,2-a]pyrimidine 30 and pyrazole[1,5-a]pyrimidine derivatives 32.
Synthesis and antioxidant assay of new nicotinonitrile analogues clubbed thiazole, pyrazole and/or pyridine ring systems
Abumelha, Hana M. A.
, (2020)
A series of novel nicotinonitrile derivatives were synthesized by hybridization with thiazole, pyrazole, and pyridine ring systems using 4-aminobenzohydrazide as link-bridge. The synthetic strategy of nicotinonitrile-thiazole analogues involves cyclizatio
Uses of ethyl benzoyl acetate for the synthesis of thiophene, pyran, and pyridine derivatives with antitumor activities
Ibrahim, Bishoy A.,Mohareb, Rafat M.
, p. 4023 - 4035 (2020/09/21)
The N-(arly)propanamide derivatives 3a,b were used for a series of heterocyclization reactions to give thiophene, pyran, and pyridine derivatives. Thus, these compounds underwent the Gewald's thiophene synthesis through their reactions with either malononitrile or ethyl cyanoacetate and elemental sulfur to afford compounds 6a-f, respectively. In addition, they were subjected through a series of multicomponent reactions (MCRs) to give pyran and fused derivatives. The reactions of 3a,b with either malononitrile or ethyl cyanoacetate gave pyridine derivatives 14a-d, respectively. The latter compounds afforded arylhydrazone derivatives 15a-m through their reactions with any of the aromatic diazonium salts 15a-c. The antitumor of the synthesized compounds against A549 (nonsmall cell lung cancer), H460 (human lung cancer), HT-29 (human colon cancer), and MKN-45 (human gastric cancer cancer) cancer cell lines together with foretinib as the positive control by a MTT assay was measured, and the results obtained showed that many compounds exhibited high potency against the six cancer cell lines.
New Thiophene Derivatives as Antimicrobial Agents
Mabkhot, Yahia Nasser,Kaal, Nahed Ahmed,Alterary, Seham,Mubarak, Mohammad S.,Alsayari, Abdulrhman,Bin Muhsinah, Abdullatif
, p. 2845 - 2953 (2019/08/26)
Phenacylbromide derivatives constitute a multilateral group of precursors for the synthesis of numerous heterocycles of organic compounds. Briefly, 5-(2-bromo-acetyl)-substituted-thiophene derivative has been used as a synthon for synthesis of new thiophene-containing compounds through the reaction with nucleophilic nitrogen compounds and thioamides. The suggested structures of the newly synthesized thiophene compounds were confirmed and assured with different spectroscopic tools and with CHN elemental analysis. Additionally, the antimicrobial activity of these thiophene compounds was recorded to investigate their potency against various types of bacteria and fungi. Results showed that these compounds exhibit significant inhibitory activity against the growth of tested bacterial and fungal strains and that some derivatives were more potent than the employed reference drugs.
Synthesis process of p-chlorophenylhydrazine hydrochloride
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Paragraph 0064-0092, (2019/10/29)
The invention relates to the technical field of organic synthesis, in particular to a synthesis process of p-chlorophenylhydrazine hydrochloride. The synthesis process comprises the following steps: (1) diazotization: mixing p-chloroaniline, strong acid and water, and adding a nitrite solution to obtain a substance A; and (2) catalytic hydrogenation: mixing the substance A with a catalyst under ahydrogen condition, and filtering the liquid to obtain the product. The process provided by the invention has the advantages of high yield and purity, environmental protection and simple operation.
Continuous flow solvent free organic synthesis involving solids (reactants/products) using a screw reactor
Sharma, Brijesh M.,Atapalkar, Ranjit S.,Kulkarni, Amol A.
supporting information, p. 5639 - 5646 (2019/10/22)
Here we report for the first-time various organic transformations such as aldol condensation, oxidation, nucleophilic substitutions, protection, acylations and coupling reactions using a mechanochemical approach at a controlled temperature using a single synthesis platform. Almost minimal solvents or solvent-free conditions are used, making it a very efficient and clean synthesis of various products. A jacketed screw reactor when operated at different temperatures (0 °C to 160 °C) and over a range of rotation speeds for changing the residence time (15 s-300 s) helped to achieve maximum conversion. This approach is also extended to the synthesis using substrates having different substitutions, heterocycles and steric hindrance.
Selective Formation of Products of Interrupted Feist-Benary Reaction under the Conditions of Hantzsch Pyrrole Synthesis
Matiichuk,Frolov,Pokhodylo,Pavlyuk,Obushak
, p. 799 - 801 (2018/07/06)
Reaction of 3-aryl-2-chloropropanal with 1-arylsulfonylpropan-2-ones in aqueous ammonia and alcohol under the conditions of Hantzsch pyrrole synthesis led to the selective formation of the products of interrupted Feist-Benary reaction, 2-(R-benzyl)-4-aryl
3-Aminopyrazolo[4,3-c]pyridine-4,6-dione as a precursor for novel pyrazolo[4,5,1-ij][1,6]naphthyridines and pyrido[4’,3’:3,4]pyrazolo[1,5-a]pyrimidines
Metwally, Nadia H.,Deeb, Emad A.
supporting information, p. 1614 - 1628 (2018/06/14)
The versatile, 3-aminopyrazolo[4,3-c]pyridine-4,6-dione (2) was synthesized and allowed to react with aldehydes, aryldiazonium chlorides, chalcones and enaminones to afford regioselectively the novel pyrazolo[4,3-c]pyridine derivatives 4a-c, pyrazolo[4,5,
