136-95-8Relevant academic research and scientific papers
Discovery of Potent Carbonic Anhydrase Inhibitors as Effective Anticonvulsant Agents: Drug Design, Synthesis, and in Vitro and in Vivo Investigations
Mishra, Chandra Bhushan,Kumari, Shikha,Angeli, Andrea,Bua, Silvia,Mongre, Raj Kumar,Tiwari, Manisha,Supuran, Claudiu T.
, p. 3100 - 3114 (2021/04/12)
Two sets of benzenesulfonamide-based effective human carbonic anhydrase (hCA) inhibitors have been developed using the tail approach. The inhibitory action of these novel molecules was examined against four isoforms: HCA I, hCA II, hCA VII, and hCA XII. Most of the molecules disclosed low to medium nanomolar range inhibition against all tested isoforms. Some of the synthesized derivatives selectively inhibited the epilepsy-involved isoforms hCA II and hCA VII, showing low nanomolar affinity. The anticonvulsant activity of selected sulfonamides was assessed using the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (sc-PTZ) in vivo models of epilepsy. These potent CA inhibitors effectively inhibited seizures in both epilepsy models. The most effective compounds showed long duration of action and abolished MES-induced seizures up to 6 h after drug administration. These sulfonamides were found to be orally active anticonvulsants, being nontoxic in neuronal cell lines and in animal models.
Multi-Step Synthesis, Physicochemical investigation and optical properties of pyrazoline derivative: A Donor-π-Acceptor chromophore
Alfaifi, S. Y.,Alimuddin,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Khan, Salman A.,Kumar, Sanjay,Obaid, Rami J.,Syed, Salauddin,Ullah, Qasim
, (2020/12/17)
The new extended π-bond pyrazoline derivative (ENTD) was prepared from heterocyclic chalcone with 2-hydrazinylbenzo[d] thiazole. The spectroscopic methods established the structure of the ENTD, and the elemental analysis established the purity of the ENTD. In ten different solvents, physicochemical ENTD parameters such as the molar absorption coefficient, transition dipole moments, Stokes shift, oscillator intensity and fluorescence quantum yield were determined to see the effect of the solvent with pyrazoline derivative (ENTD) on the basis of different polarity. In addition, the interaction of ENTD chromophore with the cationic and anionic surfactants have been studied. The intensity of fluorescence spectrum of the ENTD was found to increase with an increase in the surfactant concentration. This indicates that there is a strong interaction between ENTD and surfactants. The ENTD chromophore can therefore be used as a probe to define the surfactants' CMC.
Synthesis and photophysical investigation of (BTHN) Schiff base as off-on Cd2+ fluorescent chemosensor and its live cell imaging
Khan, Salman A.,Ullah, Qasim,Almalki, Abdulraheem S.A.,Kumar, Sanjay,Obaid, Rami J.,Alsharif, Meshari A.,Alfaifi,Hashmi, Authar Adil
, (2021/02/05)
A Schiff base, 1-[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl-naphthalen-2-ol (BTHN) have been synthesized by the condensation of 2-hydrazinobenzothiazole and 2-hydroxy-1-naphthaldehyde. Structure of BTHN has been determined with the help of spectroscopic techniques and elemental analysis. Photophysical parameters of the BTHN were studied in the different solvents of varying polarity. The photophysical parameter were largely affected by the varying polarity and absorption as well as emission spectra showed strong bathochromic shift. Further, interactions of the BTHN dye with metal ions were also explored by spectrofluorimetry and BTHN found to be an excellent off-on chemosensor for Cd2+ in DMF-H2O solution. The molecular coordination complex between BTHN with Cd2+ is 1:1, confirmed by Benesi-Hildebrand and Job-plot method. In addition, the BTHN has been effectively employed for the fluorescence imaging of cadmium ions in the living cells.
Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone
Shulga,Simurova,Shulga
, p. 364 - 368 (2021/04/13)
Abstract: The condensation of 2-amino-1,3-thiazolium perchlorates and their benzo analogs with trifluoro-acetyl-acetone in acetic acid afforded the corresponding [1,3]thiazolo[3,2-a]pyrimidinium, pyrimido[2,1-b][1,3]benzothiazolium, and naphtho[2′,1′:4,5][1,3]thiazolo[3,2-a]pyrimidinium salts as a single isomer in which the trifluoromethyl group is located in the γ-position with respect to the bridgehead nitrogen atom. The structure of the synthesized compounds was confirmed by 1H NMR spectra and elemental analyses.
Chemical Genetics Reveals a Role of Squalene Synthase in TGFβ Signaling and Cardiomyogenesis
Takemoto, Yasushi,Kadota, Shin,Minami, Itsunari,Otsuka, Shinya,Okuda, Satoshi,Abo, Masahiro,Punzalan, Louvy Lynn,Shen, Yan,Shiba, Yuji,Uesugi, Motonari
supporting information, p. 21824 - 21831 (2021/08/30)
KY02111 is a widely used small molecule that boosts cardiomyogenesis of the mesoderm cells derived from pluripotent stem cells, yet its molecular mechanism of action remains elusive. The present study resolves the initially perplexing effects of KY02111 on Wnt signaling and subsequently identifies squalene synthase (SQS) as a molecular target of KY02111 and its optimized version, KY-I. By disrupting the interaction of SQS with cardiac ER-membrane protein TMEM43, KY02111 impairs TGFβ signaling, but not Wnt signaling, and thereby recapitulates the clinical mutation of TMEM43 that causes arrhythmogenic right ventricular cardiomyopathy (ARVC), an inherited heart disease that involves a substitution of myocardium with fatty tissue. These findings reveal a heretofore undescribed role of SQS in TGFβ signaling and cardiomyogenesis. KY02111 may find its use in ARVC modeling as well as serve as a chemical tool for studying TGFβ/SMAD signaling.
Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen
, (2021/09/09)
A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles
Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives
Pandian, P.,Rajkamal, B.,Sultana, Shaheen
, p. 2755 - 2761 (2021/10/25)
The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0111-0118; 0121, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
Cobalt-catalyzed domino C-N cross-coupling reaction between phenyl(2-halo)isothiourea and aryl halide
Kondraganti, Lakshmi,Tamminana, Ramana,Nathani, Srinivasa Rao,Babu, Manabolu Surendra,Ramachandran, Dittakavi
, p. 559 - 568 (2021/02/09)
A simple route for the synthesis of 2-aminophenyl benzothiazole through domino intra and inter molecular C-N cross-coupling reaction using a cobalt catalyst under mild reaction conditions has been accomplished. The procedure is experimentally simple, general, and efficient. All the substrates readily carried out under optimized reaction conditions to provide target products in moderate to good yield.
Identification of novel GPR81 agonist lead series for target biology evaluation
Davidsson, ?jvind,Nilsson, Kristina,Br?nalt, Jonas,Andersson, Terese,Berggren, Kristina,Chen, Yantao,Fjellstr?m, Ola,Gradén, Henrik,Gustafsson, Linda,Hermansson, Nils-Olov,Jansen, Frank,Johannesson, Petra,Ohlsson, Bengt,Tyrchan, Christian,Wellner, Annika,Wellner, Eric,?lweg?rd-Halvarsson, Maria
supporting information, (2020/01/22)
GPR81 is a novel drug target that is implicated in the control of glucose and lipid metabolism. The lack of potent GPR81 modulators suitable for in vivo studies has limited the pharmacological characterization of this lactate sensing receptor. We performed a high throughput screen (HTS) and identified a GPR81 agonist chemical series containing a central acyl urea scaffold linker. During SAR exploration two additional new series were evolved, one containing cyclic acyl urea bioisosteres and another a central amide bond. These three series provide different selectivity and physicochemical properties suitable for in-vivo studies.
