- Synthesis of Certain New Thiazole and 1,3,4-Thiadiazole Derivatives via the Utility of 3-Acetylindole
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2-(2-(1-(1H-Indol-3-yl)ethylidene)-hydrazinyl)-4-substituted 5-(aryldiazenyl)thiazoles and 5-((1-(1H-indol-3-yl)ethylidene)hydrazono)-2-substituted-4-phenyl-4,5-dihydro-1,3,4-thiadiazoles were synthesized via reaction of hydrazonoyl halides and 2-(1-(1H-indol-3-yl)ethylidene)hydrazine-1-carbothioamide and alkyl 2-(1-(1H-indol-3-yl)ethylidene)hydrazine-1-carbodithioate in ethanolic triethylamine. Structures of the newly synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic route whenever possible.
- Abdelhamid, Abdou O.,Gomha, Sobhi M.,Kandeel, Saher M.
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- Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents
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In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.
- Abdel-Aziz, Hatem Abdel-Kader,Eldehna, Wagdy Mohamed,Fares, Mohamed,Elsaman, Tilal,Abdel-Aziz, Marwa Mostafa,Soliman, Dalia Hussein
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- Reaction of Triazene 1-Oxides: Novel Synthesis of Solid Arenediazonium Chlorides
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Treatment of 1,3-diaryltriazene 1-oxides with oxalyl chloride in dry toluene at room temperature gives only solid arenediazonium chlorides; however, treatment with acetyl and benzoyl chlorides does not afford the corresponding diazonium chlorides.
- Mohamed, Shaaban K.,Gomaa, Mohsen A.-M.,Nour El-Din, Ahmed M.
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- Tetracyclic compounds from 1-oxo-1,2,3,4,5,6-hexahydrocycloocta[b]indole. Synthesis of oxazolo[4′5′:8,7]cycloocta[b]indoles
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Japp-Klingmann method was used to diazotise aniline derivatives and 2-hydroxymethylenecyclooctanone 2 to obtain cyclooctan-1′,2′ -dione-1′-arylhydrazone 3 which upon acid cyclisation using kents reagent gave 1-oxo-1,2,3,4,5,6-hexahydrocycloocta[b]indole 4
- Vandana,Velumani,Prasad, K. J. Rajendra
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- New 2-pyrone-based hydrazones: Synthesis, spectral characterisation, UV–visible study and evaluation of the antiradicalar activity
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The synthesis of new 2-pyrone-based hydrazones has been prepared by the coupling of 6-methyl-2H-furo[3,2-c]pyran-3,4-dione with diazonium salts, obtained by diazotization of aniline derivatives. The structure of all compounds was established by spectrosco
- Oukacha-Hikem, Djamila,Makhloufi-Chebli, Malika,Amar, Anissa,Bouherrou, Houria,Rachedi, Yahia,Meghezzi, Hacène,Silva, Artur M. S.,Hamdi, Maamar
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- ASYMMETRIC SYNTHESIS OF α-AMINO β-HYDROXY PHOSPHONIC ACIDS VIA BINAP-RUTHENIUM CATALYZED HYDROGENATION
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BINAP-Ru catalyzed hydrogenation of configurationally labile α-amido β-keto phosphonic esters gives the (R,R)- or (S,S)-α-amido β-hydroxy phosphonic esters in a highly enantio- and diastereoselective manner.
- Kitamura, Masato,Tokunaga, Makoto,Pham, Trang,Lubell, William D.,Noyori, Ryoji
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- Electrochemical investigations of some newly synthesized arylazapyrazole derivatives
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Abstract: Three derivatives of arylazapyrazole ((E)-4-(phenyldiazenyl)-3,5-dimethyl-1H-pyrazole, (E)-4-[(4-fluorophenyl)diazenyl]-3,5-dimethyl-1H-pyrazole, and (E)-4-[(4-iodophenyl)diazenyl]-3,5-dimethyl-1H-pyrazole) were synthesized, characterized, and further investigated for their electrochemical behavior at glassy carbon electrode using cyclic voltammetry. All compounds were reduced following Ei Ci mechanism giving single cathodic peak in potential range 0 to ?2?V vs. Ag/AgCl. The plots of log iP vs. log ν showed that the electrode process is mixed adsorption-diffusion controlled. The kinetic parameters such as transfer coefficient (αn), diffusion coefficients (Do), and standard heterogeneous rate constants (ks) were determined from the electrochemical data. The values of Do were determined and found greater for the smallest among the three compounds. ks values were calculated by Laviron formalism which lies in the order of 10?2?s?1. Temperature and pH effects were studied and thermodynamic parameters such as change in free energy of activation (ΔG#), apparent activation energy (Ea), enthalpy (ΔH#), and entropy (ΔS#) of activation were determined. Negative values of Ea, ΔH#, and ΔS# imply that the electrode process needs lesser over potential with temperature rise, pre-adsorption of the analyte onto the electrode surface and the activated complex has a more organized structure than the reactants, respectively. Graphical abstract: [Figure not available: see fulltext.]
- Arshad, Nasima,Ikramullah,Aamir, Muhammad,Sher, Muhammad
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- 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
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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,
- Metwally, Nadia H.,Deeb, Emad A.
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- Polymer complexes. LXX. Synthesis, spectroscopic studies, thermal properties and antimicrobial activity of metal(II) polymer complexes
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The monomer 3-allyl-5-(phenylazo)-2-thioxothiazolidine-4-one (HL) was prepared by the reaction of allyl rhodanine with aniline through diazo-coupling reaction. Reaction of HL with Ni(II) or Co(II) salts gave polymer complexes (1–8) with general stoichiome
- Morgan, Sh. M.,El-Sonbati,El-Mogazy
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- Rates and mechanisms of the thermal solvolytic decomposition of arenediazonium ions
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Arenediazonium tetrafluoroborates have been prepared and the kinetics of solvolysis have been investigated in water, trifluoroethanol, water-trifluoroethanol mixtures, hexafluoropropan-2-ol, trifluoroacetic acid, and ethanol by a UV method. A heterolytic mechanism involving short-lived aryl cations leads to products derived from nucleophilic capture of the aryl cations by solvent or a solute. Ionic solutes in aqueous trifluoroethanol and trifluoromethoxybenzene in trifluoroethanol have no kinetic effect and neither does replacement of the tetrafluoroborate counter-ion by chloride in trifluoroethanol. Rate constants for any one compound are not very solvent dependent, the reactions generally being characterised by high enthalpies of activation and appreciably positive entropies of activation. Compounds with 4-Cl, 4-F, 4-NO2, and 4-MeO substituents proved too unreactive for kinetic studies, but for different reasons. In ethanol, a radical reaction with characteristically different activation parameters competes with the heterolytic path and leads to hydrodediazoniation (reduction) by hydrogen atom abstraction from the CH2 group of ethanol.
- Canning, Peter S. J.,McCrudden, Katharine,Maskill, Howard,Sexton, Brian
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- New Thiophene Derivatives as Antimicrobial Agents
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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.
- Mabkhot, Yahia Nasser,Kaal, Nahed Ahmed,Alterary, Seham,Mubarak, Mohammad S.,Alsayari, Abdulrhman,Bin Muhsinah, Abdullatif
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- Ligand-free Suzuki-Miyaura cross-coupling reactions of aryltriazenes with arylboronic acids
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The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd(OAc)2 without added ligands has been achieved for the first time. The reactions performed at room temperature under an argon atmosphere give biaryls in good to excellent yields. It is noteworthy that the reactions were conducted under mild and ligand-free conditions. The boron trifluoride induced Suzuki-Miyaura cross-coupling of aryltriazenes with arylboronic acids catalyzed by Pd(OAc) 2 without added ligands has been achieved for the first time. Copyright
- Nan, Guangming,Zhu, Fanghua,Wei, Zhijun
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- Selective Formation of Products of Interrupted Feist-Benary Reaction under the Conditions of Hantzsch Pyrrole Synthesis
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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
- Matiichuk,Frolov,Pokhodylo,Pavlyuk,Obushak
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- Facile Synthesis of Pyrazolo[3,4-c]pyrazoles Bearing Coumarine Ring as Anticancer Agents
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In the present study, 2-(2-oxo-2H-chromene-3-carbonyl)-5-phenyl-2,4-dihydro-3H-pyrazol-3-one was prepared and reacted with various hydrazonoyl halides to give a series of 2-(2-oxo-2H-chromene-3-carbonyl)-5-phenyl-4-((2-phenylhydrazono)methyl)-2,4-dihydro-3H-pyrazol-3-one in good yield. Cyclization of the latter hydrazone with POCl3 yielded the respective 3-(3-phenyl- 4,6-disubstituted-1,6-dihydropyrazolo[3,4-c]pyrazole-1-carbonyl)-2H-chromen-2-ones. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 4e, 4c, and 4d with IC50 equal 0.92?±?0.22, 1.43?±?0.19, and 2.17?±?0.21?μM, respectively.
- Gomha, Sobhi M.,Abdel-aziz, Hassan M.,El-Reedy, Ahmed A. M.
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- Design, synthesis, and molecular docking study of novel heterocycles incorporating 1,3,4-thiadiazole moiety as potential antimicrobial and anticancer agents
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A new series of 5-(3,5-dinitrophenyl)-1,3,4-thiadiazole derivatives were prepared and evaluated for their in vitro antimicrobial, antitumor, and DHFR inhibition activity. Compounds 9, 10, 13, and 16 showed strong and broad-spectrum antimicrobial activity comparable to Amoxicillin and Fluconazole as positive antibiotic and antifungal controls, respectively. Compounds 6, 14, and 15 exhibited antitumor activity against four human cancer cell lines, CCRF-CEM leukemia, HCT-15 colon, PC-3 prostate, and UACC-257 melanoma cell lines using Doxorubicin as a reference drug. Compounds 10, 13, 14, and 15 proved to be the most active DHFR inhibitors with an IC50 range of 0.04 ± 0.82–1.00 ± 0.85 μM, in comparison with Methotrexate (IC50 = 0.14 ± 1.38 μM). The highly potent DHFR inhibitors shared a similar molecular docking mode and made a critical hydrogen bond and arene?arene interactions via Ser59 and Phe31 amino acid residues, respectively.
- El-Naggar, Mohamed,Sallam, Hanan A.,Shaban, Safaa S.,Abdel-Wahab, Salwa S.,Amr, Abd El-Galil E.,Azab, Mohammad E.,Nossier, Eman S.,Al-Omar, Mohamed A.
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- A Novel Synthesis of Some 1,4-Phenylene-bis-heterocyclic Derivatives and of Some Pyran, Pyrano[2,3-c]pyrazole, and Pyrano[2,3-d]pyrimidine Derivatives [1]
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p-Diacetyl benzene 1 undergoes bromination to afford p-bromoacetyl phenacyl bromide 2. Compound 2 reacts with twofold excess of malononitrile to afford 2-{2-[4-(3,3-Dicyanopropionyl)-phenyl]-2-oxo-ethyl}-malononitrile 3. Compound 3 could be cyclized to af
- Abdelrazek,Helal,Hebishy,Hassan
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- A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes
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A series of novel substituted-azo dyes 8-(aryldiazenyl)quinolin-5-ol (5a-i) were synthesized by the coupling reaction of 5-hydroxyquinoline with diazotized aniline derivatives in the presence of NaNO2 in HCl/H2O mixture. The study of
- Coelho, Paulo J.,Lup, Andrew Ng Kay,Mahon, Peter J.,Pesyan, Nader Noroozi,Ramezanitaghartapeh, Mohammad,Raposo, M. Manuela M.,Rashidnejad, Hamid,Soltani, Alireza
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- Preparation method of monocyclic or polycyclic compound containing pyrrole ring
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The invention discloses a preparation method of a monocyclic or polycyclic compound containing a pyrrole ring. An enamine compound is used as a raw material and is continuously subjected to diazotization, reduction and cyclization synthesis with a carbony
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Paragraph 0028-0030; 0031-0032
(2021/05/15)
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- INHIBITORS OF RECEPTOR INTERACTING PROTEIN KINASE I FOR THE TREATMENT OF DISEASE
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Disclosed herein are compounds which inhibit RIPK1, pharmaceutical compositions, and methods of treatment of RIPK1-mediated diseases, such as neurodegenerative disorders, inflammatory disorders, and cancer.
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Paragraph 0518-0520
(2021/05/29)
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- Synthetic method for preparing 5-aminobenzimidazolone
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The invention discloses a synthesis method for preparing 5-aminobenzimidazolone (TM), which comprises the following steps: firstly, carrying out diazotization reaction on aniline to prepare aniline diazonium salt; secondly, coupling the aniline diazonium salt with o-phenylenediamine to generate an azo compound, and carrying out a reaction on the azo compound and urea under the catalysis of concentrated sulfuric acid to generate an azobenzimidazolone compound, and subjecting the azobenzimidazolone compound to a hydrogenation reduction reaction to obtain the target compound 5-aminobenzimidazolone. The method disclosed by the invention is simple in process, high in selectivity and high in product yield, all used reactants are utilized, and the method has very high atom economy. The use of a nitration reagent concentrated nitric acid is avoided, the wastewater and the generation of salt in the wastewater are greatly reduced, and the method is a green production process. In addition, the hydrocracking reduction operation is simple, no other iron mud such as iron powder reduction is generated, no waste residue is basically generated, the quality of a finished product is obviously improved, filter-pressing rinsing water can be repeatedly used for more than multiple times, the cost is reduced, and the environmental pollution is reduced.
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Paragraph 0016; 0031-0033; 0042-0044
(2021/07/17)
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- Uses of ethyl benzoylacetate for the synthesis of thiophene, thiazole, pyridine, and pyran derivatives with antitumor activities
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The reaction of ethyl benzoylacetate with malononitrile in an oil bath at 120°C gave the condensation product 3. The latter compound underwent a series of heterocyclization to give thiophene, thiazole, pyridine, and pyran derivatives. The structures of the synthesized products were established on the basis of analytical and spectral data. The antitumor evaluation of the newly synthesized products against the six cancer cell lines namely human gastric cancer (NUGC and HR), human colon cancer (DLD1), human liver cancer (HA22T and HEPG2), human breast cancer (MCF), nasopharyngeal carcinoma (HONE1), and normal fibroblast cells (WI38) indicated that many compounds expressed high inhibition against the six cancer cell lines. Compounds 3, 8a, 8c, 14b, 16b, 16c, 16d, 19a, 19b, 20a, 22a, 27b, and 28a were the most cytotoxic compounds among the tested compounds.
- Mohareb, Rafat M.,Mostafa, Bahaa M.
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- Uses of ethyl benzoyl acetate for the synthesis of thiophene, pyran, and pyridine derivatives with antitumor activities
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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.
- Ibrahim, Bishoy A.,Mohareb, Rafat M.
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p. 4023 - 4035
(2020/09/21)
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- Synthesis method for selective heterochromous isomer of wave absorption material 2,4-di(phenyl azo) m-dihydroxybenzene
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The invention discloses a synthesis method for a selective heterochromous isomer of a wave absorption material 2,4-di(phenyl azo) m-dihydroxybenzene. The synthesis method comprises the following steps: enabling m-dihydroxybenzene to react with potassium h
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Paragraph 0025
(2019/10/17)
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- Continuous flow solvent free organic synthesis involving solids (reactants/products) using a screw reactor
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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.
- Sharma, Brijesh M.,Atapalkar, Ranjit S.,Kulkarni, Amol A.
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supporting information
p. 5639 - 5646
(2019/10/22)
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- (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides as tubulin polymerization inhibitors: Structure-based bioisosterism design, synthesis, biological evaluation, molecular docking and in silico ADME prediction
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A series of (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides have been synthesized and evaluated for their anticancer activity in human hepatocellular liver carcinoma HepG2 and breast adenocarcinoma MCF-7 cell lines. Among all the test
- Wang, Guangcheng,Peng, Zhiyun,Peng, Shanshan,Qiu, Jie,Li, Yongjun,Lan, Yanyu
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supporting information
p. 3350 - 3355
(2018/09/12)
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- Replacement of a Naphthalene Scaffold in Kelch-like ECH-Associated Protein 1 (KEAP1)/Nuclear Factor (Erythroid-derived 2)-like 2 (NRF2) Inhibitors
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Activators of nuclear factor-erythroid 2-related factor 2 (NRF2) could lead to promising therapeutics for prevention and treatment of oxidative stress and inflammatory disorders. Ubiquitination and subsequent degradation of the transcription factor NRF2 is mediated by Kelch-like ECH-associated protein-1 (KEAP1). Inhibition of the KEAP1/NRF2 interaction with small molecules leads to NRF2 activation. Previously, we and others described naphthalene-based NRF2 activators, but the 1,4-diaminonaphthalene scaffold may not represent a drug-like scaffold. Paying particular attention to aqueous solubility, metabolic stability, potency, and mutagenicity, we modified a previously known, naphthalene-based nonelectrophilic NRF2 activator to give a series of non-naphthalene and heterocyclic scaffolds. We found that, compared to previously reported naphthalene-based compounds, a 1,4-isoquinoline scaffold provides a better mutagenic profile without sacrificing potency, stability, or solubility.
- Richardson, Benjamin G.,Jain, Atul D.,Potteti, Haranatha R.,Lazzara, Phillip R.,David, Brian P.,Tamatam, Chandra R.,Choma, Ewelina,Skowron, Kornelia,Dye, Katherine,Siddiqui, Zamia,Wang, Yue-Ting,Krunic, Aleksej,Reddy, Sekhar P.,Moore, Terry W.
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p. 8029 - 8047
(2018/09/12)
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- Containing chrysanthemic acid structure pyrazole compound and its preparation method and use thereof
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The invention discloses a pyrazole compound containing chrysanthemic acid structure and a preparation method and purpose of the pyrazole compound with the general structural formula (I). The definition of each substituent group in the general structural formula (I) is showed in the description and claims. The pyrazole compound is good in insect killing effect, simple in production process and high in yield.
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Paragraph 0037; 0038; 0039
(2018/11/03)
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- PROCESS FOR THE SYNTHESIS OF ARYLDIAZONIUM SALTS USING NITROGEN OXIDES IN OXYGEN-CONTAINING GAS STREAMS, ESPECIALLY FROM INDUSTRIAL WASTE GASES
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The present invention relates to a process for the synthesis of aryldiazonium salts using nitrogen oxides in oxygen-containing gas streams, especially from industrial waste gases.
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Page/Page column 35; 36; 37; 38; 39
(2017/06/30)
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- Synthesis and characterization of new pyrazole-based thiazoles
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A series of new 5-(heteroaryldiazenyl)thiazole incorporating pyrazole moiety have been synthesized through coupling of the thiazole with the appropriate heteroaryldiazonium salts. The newly synthesized compounds were characterized by elemental analysis, s
- Abdelhamid, Abdou O.,Gomha, Sobhi M.
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supporting information
p. 1409 - 1414
(2017/07/25)
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- Total chemical synthesis method of adenine
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The invention relates to a total chemical synthesis method of adenine. The method comprises the following steps of: 1) dissolving primary amine in strong-acid solution, dripping sodium nitrite solution to prepare diazonium salt, adding malononitrile for dissolving, and dripping alkaline solution to regulate a pH value of reaction solution and generate coupling reaction, thereby obtaining an azo compound; 2) adding the azo compound into formamide, and introducing liquid ammonia, heating to carry out high-temperature condensation and cyclization reaction, thereby obtaining a pyrimidine-azo compound; 3) dissolving the pyrimidine-azo compound into water, adding a catalyst, and introducing hydrogen for hydrogenation, thereby obtaining 4,5,6-triamidopyrimidine; and 4) dissolving the 4, 5, 6-triamidopyrimidine into the formamide to carry out high-temperature cyclization with the formamide, thereby obtaining an adenine crude product, and after recrystallization, obtaining white crystalline powder, i.e., a high-purity refined adenine product. The total chemical synthesis method has the advantages that water is used as a solvent in the step 1), and solvents used in the steps 2), 3) and 4) can be repeatedly used, so that the 'three wastes' are fewer, and the environment-friendly effect is achieved; and the total yield is 64.75% (calculated according to the amount of malononitrile), and the cost is low, so that the industrialization is easy and the economic benefit is obvious.
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Paragraph 0017
(2017/08/29)
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- Design, synthesis and anticancer activity of some novel 5-(4-methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one derivatives
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New pyrazole derivatives were designed and synthesized by the reaction of 5-(4-methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-one (4) or 5-(4-methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (5) with series of aldehydes, substituted amines, isatins and phenylisothiocynate to yield 6a-j, 7a-k, 9a-d and 10a-b, respectively. The synthesized compounds were examined in vitro for their anti-tumor activities against HepG-2, PC-3 and HCT-116 human carcinoma cell lines using MTT assay. Eight compounds showed good anticancer activities against HCT-116 carcinoma cells and five compounds showed good anticancer activities against PC-3 cancer cells but all the compounds showed weak or no anticancer activities against HepG-2 liver cancer.
- Fathy, Usama,Gouhar, Rasha S.,Awad, Hanem M.
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p. 1427 - 1436
(2017/10/23)
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- Synthesis method of solvent yellow 124
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The invention discloses a synthesis method of solvent yellow 124. The synthesis method comprises the following steps: diazotizing aniline serving as a raw material to obtain chloridized diazonium benzene, carrying out reaction on N-ethyl-N-hydroxyethylaniline and treated metal sodium particles to obtain sodium alcoholate, carrying out aldolization on the sodium alcoholate, and carrying out coupling reaction on the sodium alcoholate subjected to the aldolization and the chloridized diazonium benzene to obtain the solvent yellow 124. The reaction line is high in synthesis yield, and a prepared product is high in purity and contains few impurities; meanwhile, the reaction conditions are mild, and a middle body is high in purity and stable; continuous or intermittent operation can be performed; a technical support is supplied to industrial continuous production.
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Paragraph 0036; 0037; 0046; 0047; 0056; 0057; 0066; 0067
(2017/08/29)
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- Influence of intramolecular charge transfer and nuclear quantum effects on intramolecular hydrogen bonds in azopyrimidines
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Intramolecular hydrogen bonds (IMHBs) in 5-azopyrimidines are investigated by NMR spectroscopy and DFT computations that involve nuclear quantum effects. A series of substituted 5-phenylazopyrimidines with one or two hydrogen bond donors able to form IMHB
- Bartova, Katerina,?echova, Lucie,Prochazkova, Elis?a,Socha, Ondrěj,Janeba, Zlatko,Drac nsky, Martin
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p. 10350 - 10359
(2018/04/14)
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- Halobenzene cyanopyrazole compound containing purine structure as well as preparation method and application
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The invention discloses a halobenzene cyanopyrazole compound containing a purine structure as well as a preparation method and an application. The halobenzene cyanopyrazole compound is a compound with a general structure (I) as shown in the specification or a pharmaceutically acceptable salt thereof. The compound is low in dosage, good in insecticidal efficacy, simple in technique, low in cost and wide in market prospect.
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Paragraph 0035
(2016/10/31)
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- Synthesis and biological evaluation of novel fused triazolo[4,3-a] pyrimidinones
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The reaction of thione 3 or its 2-methylthio derivative 4 with hydrazonoyl halides 5a-l, in the presence of triethylamine, yielded the corresponding triazolo[4,3- a]pyrimidin-5(1H)-ones 8a-l. The structure of compounds 8a-l was further confirmed by the re
- Abbas, Ikhlass,Gomha, Sobhi,Elneairy, Mohamed,Elaasser, Mahmoud,Mabrouk, Bazada
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p. 510 - 531
(2015/08/06)
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- Fluoride-responsive organogel containing azobenzyl and cholesterol units
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In this paper, two new cholesterol-based compounds O1 and O2 were designed and synthesized. The compound O2 could selectively gel in 1,4-dioxane with porous ribbon structure. The aggregation mode of O2 molecules were characterized by SEM, IR, UV-vis and X
- Geng, Lijun,Feng, Guoliang,Wang, Shiguang,Yu, Xudong,Xu, Zhice,Zhen, Xiaoli,Wang, Tao
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supporting information
p. 24 - 28
(2015/03/05)
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- Optical evodiamine derivatives: Asymmetric synthesis and antitumor activity
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Evodiamine and its derivatives have an asymmetric center at the C13b position. Herein, isomers of evodiamine derivatives 2 and 3 were obtained by straightforward asymmetric total synthesis. Their inhibitory activities toward topoisomerases I and II and th
- Li, Zhen-Gang,Dong, Guo-Qiang,Wang, Sheng-Zheng,Miao, Zhen-Yuan,Yao, Jian-Zhong,Zhang, Wan-Nian,Sheng, Chun-Quan
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p. 267 - 271
(2015/04/14)
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- An emissive and pH switchable hydrazone-based hydrogel
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A serendipitous discovery has led to a new hydrazone-based low molecular weight fluorescent super-hydrogelator. The gelation and emission properties can be switched "ON" and "OFF" using pH, enabling the sensing of biogenic amines emanating from spoiled cod.
- Qian, Hai,Aprahamian, Ivan
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supporting information
p. 11158 - 11161
(2015/07/07)
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- Synthesis of novel benzimidazole and benzothiazole derivatives
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1-(Benzothiazol-2-yl)-2-phenylsulfonyl-1-ethanone (1) and 1-(1-methyl-1H-benzimidazol-2-yl)-2-(phenylsulfonyl)-1-ethanone (2) were used as potential scaffolds for biologically interesting azoloazine derivatives via their reaction with the diazonium salts
- Darweesh, Ahmed F.,Mekky, Ahmed E. M.,Salman, Amani A.,Farag, Ahmad M.
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p. 113 - 125
(2014/02/14)
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- PYRAZOLO[4,3-D]PYRIMIDIN-7(6H)-ONE DERIVATIVES AS PDE9 INHIBITORS
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Pyrazolo[4,3-d]pyrimidin-7(6H)-one derivatives represented by the general formula (I), wherein R1 represents hydrogen atom or methyl; when R1 represents hydrogen atom, then R2 represents cyclopentyl, tetrahydropyranyl, cyclohexyl, or cyclohexyl substituted with 1 or 2 halogen atoms; when R1 represents methyl, then R2 represents cyclopentyl; R3 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, and OCH3; and 6- to 10-membered heteroaryl with 1 to 3 heteroatoms selected independently form O, N and S; and Q represents C1-C3-alkylene group, which is unsubstituted or substituted with 1 to 3 C1-C3-alkyl groups; and their salts. The compounds are PDE9A inhibitors useful as m edicaments, in particular for treatment of cognitive function disorders and neurodegenerative diseases
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Page/Page column 27
(2014/03/21)
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- Synthesis of progesterone derivatives and evaluation of their efficiency as pneumococcal vaccines
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Progesterone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1, through its reaction with active methylene derivatives, gave the condensate derivatives 3a, b. The latter compounds underwent heterocyclization reaction
- Mohareb, Rafat M.,Al Farouk, Fatma O.,Sherif, Sherif M.,Karaghiosoff, Konstantin
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p. 3165 - 3177
(2014/05/06)
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- Heterocyclic ring extension of estrone: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives
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The one pot reaction of estrone with the aromatic aldehydes 2a-c and either of malononitrile or ethyl cyanoacetate afforded the fused pyran derivatives 4a-f. On the other hand, carrying the same reaction using thiourea instead of the cyanomethylene reagent gave the fused pyrimidine derivatives 6a-c. The latter compounds reacted with phenacyl bromide to give the thiazolo[3,2-a] pyrimidine derivatives 8a-c. The reaction of the title compound with bromine gave the monobromo derivative 13 which in turn reacted with either thiourea or cyanothioacetamide to give the thiazole derivatives 14 and 16, respectively. The cytotoxicity of the newly synthesized products was evaluated against six human cancer and normal cell lines where the results showed that compounds 4c, 4f, 6b, 8b, 8c, 10, 13, 16, 18c and 19c exhibited optimal cytotoxic effect against the cancer cell lines, with IC50's in the nM range.
- Mohareb, Rafat M.,Al-Omran, Fatima,Azzam, Rasha A.
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- Enaminonitriles in heterocyclic synthesis: A route to 1,3-diaryl-4- Aminopyrazole derivatives
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Benzylcyanide and 4-nitrobenzylcyanide condensed with triethyl orthoformate and piperidine or morpholine to yield 2-Aryl-2-piperidinyl or 2-morpholinylacrylonitriles. These coupled with aromatic diazonium salts to yield the 2-Arylhydrazno-2-Arylethane nit
- Medrasi, Hanadi Y.,Al-Sheikh, Mariam Abdullah,Salaheldin, Abdellatif Mohamed
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p. 535 - 544
(2013/03/13)
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- Synthesis, characterization, and electrochemical study of some novel, azo-containing Schiff bases and their Ni(II) complexes
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Five novel azo-azomethine ligands with NN'OS coordination spheres were prepared by reaction of methyl-2-{N-(2′-aminoethane)}-amino-1- cyclopentenedithiocarboxylate (Hcden) with (E)-2-hydroxy-5-(phenyldiazenyl) benzaldehyde and its substituted derivatives
- Menati, Saeid,Azadbakht, Azadeh,Azadbakht, Reza,Taeb, Abbas,Kakanejadifard, Ali
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p. 499 - 506
(2013/07/27)
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- The first "kuhn verdazyl" ligand and comparative studies of its PdCl2 complex with analogous 6-oxoverdazyl ligands
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The synthesis and characterization of two new N,N′-diarylverdazyl radical ligands and their corresponding PdCl2 complexes are described. One of the two radicals is of the "Kuhn verdazyl" structure type and was made by adaptation of standard syn
- Johnston, Cooper W.,McKinnon, Stephen D. J.,Patrick, Brian O.,Hicks, Robin G.
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p. 16829 - 16836
(2013/12/04)
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- Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes
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Imidazolium based nitrite ionic liquid containing trimethoxysilyl group was prepared from the reaction of N-methylimidazole and (3-chloropropyl) trimethoxysilane. This ionic liquid was immobilized on silica covalently to give nanoparticles with the imidazolium nitrite moiety remaining intact. The diazotization reaction was performed as a model reaction to examine the activity of these nanoparticles as a nitrosonium source. Excellent performance was exhibited in the diazotization reaction of various aniline derivatives in the presence of HCl under mild heterogeneous conditions (room temperature and short reaction time). In-situ coupling of diazonium salts to a range of tertiary anilines, phenols and naphthols afforded the requisite azo dyes in good yield, using standard experimental procedures.
- Valizadeh, Hassan,Amiri, Mohammad,Hosseinzadeh, Fatemeh
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experimental part
p. 1308 - 1313
(2012/03/27)
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- 4-Thiazolidinones in heterocyclic synthesis: Synthesis of novel enaminones, azolopyrimidines and 2-arylimino-5-arylidene-4-thiazolidinones
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The 4-thiazolidinones 3a-d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a-p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13-18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work.
- Behbehani, Haider,Ibrahim, Hamada Mohamed
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experimental part
p. 6362 - 6385
(2012/08/28)
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- Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
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Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis. The Royal Society of Chemistry 2012.
- Fang, Jie,Zhou, Jianguang
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supporting information; experimental part
p. 2389 - 2391
(2012/04/11)
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- Synthesis and antimicrobial activity of new Thiazolidinone derivatives with the use of γ-ferrite catalyst
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A series of compounds were synthesized from 3, 3?- (pyridine-2, 6- diyl) bis (2-phenylthiazolidin-4-one (1), which was prepared from a one-pot three component condensation reaction of 2, 6-diamino pyridine, benzaldehyde and thioglycolic acid in the presen
- Shrivastava,Seelam, Nareshvarma,Rai, Rachana
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experimental part
p. 825 - 831
(2012/08/29)
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- Synthesis and antimicrobial effects of 1,3,5-substituted phenyl formazans
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In this study, novel formazans with various substituents on 1,3,5-phenyl rings were synthesized and their structures were elucidated with the use of elemental analysis, mass,1H NMR,13C NMR, IR, UV-VIS spectra. Also, antimicrobial effects of formazans were tested against selected microorganism, Staphylococus aureus, S. epidermidis, S. saprophyticus, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae. Moreover, the antiyeast effects of the formazans are seen on the Candida kefir, C. glabrata, C. tropicalis, Cryptococcus neofarmans, Saccharomyces cerevisiae. In the present study, it was generally observed that the formazans were very active against Candida kefir, C. tropicalis, Cryptococcus neofarmans and Saccharomyces cerevisiae.
- Uraz, Guven,Yilmaz, Ebru,Tezcan, Habibe,Porsuk, Nesrin,Imamoglu, Gamze,Kartli, Onur Savas
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experimental part
p. 1924 - 1926
(2012/09/07)
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- Reaction with hydrazonoyl halides 64: Synthesis of some new triazolino[4,3-a]pyrimidines, 1,3,4-thiadiazoles, and 5-arylazothiazoles
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2,3-Dihydro-1,3,4-thiadiazoles, 2,3-dihydro-1,3,4-selenadiazoles, and triazolino[4,3-a]pyrimidines containing benzofuran moiety were prepared from the reaction of 2-(2-phenylhydrazono)-1-(5-bromobenzofuran-2-yl)-2-chloroethanone with each of potassium thi
- Abdelhamid, Abdou O.,Fahmi, Abdelgawad A.,Baaui, Basma S.
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p. 1098 - 1107,10
(2020/10/15)
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- Heterocyclizations of pregnenolone: Novel synthesis of thiosemicarbazone, thiophene, thiazole, thieno[2,3-b]pyridine derivatives and their cytotoxicity evaluations
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Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1 through its reaction with 4-phenyl-3-thiosemicarbazide gave the thiosemicarbazone derivative 3. The latter compound underwent heterocyclization reactions
- Mohareb, Rafat M.,Wardakhan, Wagnat W.,Elmegeed, Gamal A.,Ashour, Rehab M.S.
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p. 1560 - 1569
(2013/01/15)
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- Reassignment of the structures of products produced by reactions of the product believed to be 2-(1-phenyl-2-thiocyanatoethylidene)-malononitrile with electrophiles
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The reactivity of the product believed to be 2-(1-phenyl-2- thiocyanatoethylidene) malononitrile toward a variety of electrophilic and nucleophilic reagents is reported.
- Al-Mousawi, Saleh Mohammed,Moustafa, Moustafa Sherief,Elnagdi, Mohamed Hilmy
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experimental part
p. 3456 - 3468
(2011/06/26)
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- Novel synthesis of hydrazide-hydrazone derivatives and their utilization in the synthesis of coumarin, pyridine, thiazole and thiophene derivatives with antitumor activity
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The reaction of cyanoacetyl hydrazine (1) with 3-acetylpyridine (2) gave the hydrazide-hydrazone derivative 3. The latter compound undergoes a series of heterocyclization reactions to give new heterocyclic compounds. The antitumor evaluation of the newly
- Mohareb, Rafat M.,Fleita, Daisy H.,Sakka, Ola K.
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experimental part
p. 16 - 27
(2011/03/23)
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