1201-93-0Relevant academic research and scientific papers
Sulfonamide-based ring-fused analogues for CAN508 as novel carbonic anhydrase inhibitors endowed with antitumor activity: Design, synthesis, and in vitro biological evaluation
Said, Mohamed A.,Eldehna, Wagdy M.,Nocentini, Alessio,Fahim, Samar H.,Bonardi, Alessandro,Elgazar, Abdullah A.,Kry?tof, Vladimír,Soliman, Dalia H.,Abdel-Aziz, Hatem A.,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
, (2020)
In the present study, we report the design and synthesis of novel CAN508 sulfonamide-based analogues (4, 8a-e, 9a-h and 10a-e) as novel carbonic anhydrase (CA) inhibitors with potential CDK inhibitory activity. A bioisosteric replacement approach was adop
Synthesis, characterization, antimicrobial activity, 3D-QSAR, DFT, and molecular docking of some ciprofloxacin derivatives and their copper(II) complexes
Khalil, Tarek E.,El-Dissouky, Ali,Al-Wahaib, Dhuha,Abrar, Nada M.,El-Sayed, Doaa S.
, (2020)
Six new derivatives of ciprofloxacin compounds and their copper(II) complexes were synthesized, characterized by spectroscopic methods (ultraviolet–visible [UV–vis], Fourier transform infrared [FTIR], nuclear magnetic resonance [NMR], mass spectrometry [M
Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors
Kumar, Rajiv,Vats, Lalit,Bua, Silvia,Supuran, Claudiu T.,Sharma, Pawan K.
, p. 545 - 551 (2018)
In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.
SLC-0111 enaminone analogs, 3/4-(3-aryl-3-oxopropenyl) aminobenzenesulfonamides, as novel selective subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform IX
Eldehna, Wagdy M.,Abo-Ashour, Mahmoud F.,Berrino, Emanuela,Vullo, Daniela,Ghabbour, Hazem A.,Al-Rashood, Sara T.,Hassan, Ghada S.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Alharbi, Amal,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, p. 549 - 558 (2019)
SLC-0111, an ureido substituted benzenesulfonamide, is a selective carbonic anhydrase (CA, EC 4.2.1.1) IX inhibitor that is currently in Phase I/II clinical trials for the treatment of advanced hypoxic tumors complicated with metastases. Herein we report
Synthesis and Biological Activity of Some Novel Aryl-Substituted 1,3,4-Oxadiazole Mannich Bases Containing Pyrimidine Rings
Shen, Shengqiang,Sun, Xiaohong,Liu, Yuanfa,Chen, Bang,Jin, Ruyi,Ma, Haixia
, p. 1296 - 1301 (2015)
A series of novel Mannich base derivatives (E1-E15) of 5-aryl-1,3,4-oxadiazole-2-thione with substituted pyrimidine were synthesized and characterized by elemental analysis, IR, 1H-NMR. The antifungal activities of these compounds were also originally studied. The results showed that most of the title compounds exhibited relatively good fungicidal activities. Especially compounds E8 and E13 showed better antifungal activity than comparison compound hymexazol. The relationship of structure and activity revealed that the presence of the methyl group at four and six positions of pyrimidine ring remarkably enhanced the antifungal activity of title compounds.
Synthesis and Cation Recognition Study of Novel Benzo Crown Ether Functionalized Enamine Derivatives
Patil, Dayanand R.,Chandam, Dattatraya R.,Mulik, Abhijeet G.,Jagdale, Suryabala D.,Patil, Prasad P.,Deshmukh, Madhukar B.
, p. 1902 - 1911 (2015)
A novel series of benzo crown ether (dibenzo 18-crown-6 ether, benzo 18-crown-6 ether, and benzo 15-crown-5 ether) functionalized enamines derivatives from amino benzo crown ether (4-amino dibenzo 18-crown-6 ether, 4-amino benzo 18-crown-6 ether, 4-amino
Facile Synthesis of Some New Pyrazole-Based 2-Thioxo-4-thiazolidinone
Metwally, Nadia Hanafy,El-Doseky, Ibrahim Adel
, p. 2683 - 2690 (2015)
5-Ethoxymethylene-2-thioxo-4-thiazolidinone (1) reacts with hydrazine hydrate at room temperature to afford 5-(hydrazinylmethylene)-2-thioxo-4-thiazolidinone (3). Compound 3 condensed with different aromatic aldehydes 6a-d in ethanol in the presence of a few drops of piperidine to give the corresponding Schiffs bases 7a-d. On the other hand, compound 3 reacts with o-hydroxybenzaldehyde derivatives 8a and 8b in refluxing ethanol catalyzed by a few drops of piperidine to yield 1H-inadzolyl-2-thioxo-4-thiazolidinones 9a and 9b. Reaction of compound 3 with α-ketoesters 10a and 10b or α-diketones 10c-e in refluxing glacial acetic acid furnished the pyrazolyl-2-thioxo-4-thiazolidinone derivatives 11a-e. Also, compound 3 reacts with some different enaminones 12a-f in refluxing glacial acetic acid to afford the new pyrazolyl-2-thioxo-4-thiazolidinone derivatives 13a-f. Pyrazoles 15a-d was obtained via reaction of compound 3 with chalcones 14a-d in dimethylformamide (DMF). The structures of all the newly synthesized products were confirmed on the basis of their elemental and spectral data, and a plausible mechanism has been postulated to account for their formation.
One-pot synthesis of enaminones using gold's reagent
Saleh, Tamer S.,Al-Omar, Mohamed A.,Abdel-Aziz, Hatem A.
, p. 483 - 486 (2010)
Enaminones were efficiently prepared via modification for Gupton method, which depends on carrying out the latter procedure in one step reaction, avoiding the isolation of [3-(dimethylamino)-2-azaprop-2-en-1-ylidene] dimethylammonium chloride (Gold's reag
Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones
Khanikar, Shilpika,Kaping, Shunan,Helissey, Philippe,Joshi, Prince,Shaham, Salique Hassan,Mishra, Shikha,Srivastava, Mrigank,Tripathi, Renu,Vishwakarma, Jai N.
, p. 665 - 678 (2021)
In the present study, a novel series of side chain-modified quinoline β-enaminones were synthesized in good-to-excellent yields. The structures of all the synthesized compounds have been established with the help of spectral and analytical data and also b
Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones
Zhang, Zhenlei,Yang, Jiusi,Wu, Kairui,Yu, Renjie,Bu, Jiping,Huang, Zijun,Li, Shaoke,Ma, Xiantao
supporting information, (2021/12/20)
We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.
