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Multi-Step Synthesis, Physicochemical investigation and optical properties of pyrazoline derivative: A Donor-π-Acceptor chromophore
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.
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)

Synthesis and photophysical investigation of (BTHN) Schiff base as off-on Cd2+ fluorescent chemosensor and its live cell imaging
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.
Khan, Salman A.,Ullah, Qasim,Almalki, Abdulraheem S.A.,Kumar, Sanjay,Obaid, Rami J.,Alsharif, Meshari A.,Alfaifi,Hashmi, Authar Adil
(2021/02/05)

Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone
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.
Shulga,Simurova,Shulga
p. 364 - 368
(2021/04/13)

Chemical Genetics Reveals a Role of Squalene Synthase in TGFβ Signaling and Cardiomyogenesis
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.
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)

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
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
Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen
(2021/09/09)

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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.
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(2021/05/29)

Discovery of Potent Carbonic Anhydrase Inhibitors as Effective Anticonvulsant Agents: Drug Design, Synthesis, and in Vitro and in Vivo Investigations
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.
Mishra, Chandra Bhushan,Kumari, Shikha,Angeli, Andrea,Bua, Silvia,Mongre, Raj Kumar,Tiwari, Manisha,Supuran, Claudiu T.
p. 3100 - 3114
(2021/04/12)

Cobalt-catalyzed domino C-N cross-coupling reaction between phenyl(2-halo)isothiourea and aryl halide
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.
Kondraganti, Lakshmi,Tamminana, Ramana,Nathani, Srinivasa Rao,Babu, Manabolu Surendra,Ramachandran, Dittakavi
p. 559 - 568
(2021/02/09)

Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives
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.
Pandian, P.,Rajkamal, B.,Sultana, Shaheen
p. 2755 - 2761
(2021/10/25)

Design, synthesis and antimicrobial study of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-diones through ketene–imine cycloaddition reaction
The present study deals with the synthesis of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives from the reaction of 3-(1,3-benzothiazol-2-ylimino)-1,3-dihydro-2H-indol-2-one derivatives with chloroacetyl chloride in the presence of triethyl-amine (TEA). The mechanism involved simple acid or base catalysed reaction through the formation of Schiff base followed by cyclisation via ketene–imine cycloaddition reaction. All synthesized compounds were characterized by FT-IR,1H-NMR,13C-NMR, and elemental analysis. The antimicrobial activities of the synthesized derivatives 5a-5g were examined via Micro Broth Dilution method against bacterial strains Bacillius subtilis, Staphylcoccus aureus, E. coli, P. aeruginosa, and fungal strain Candida albicans for determining MIC values. Ampicillin, chloramphenicol, and griseofulvin were used as standard drugs. The MIC values for antimicrobial activity of synthesized compounds were examined using Micro Broth Dilution method. Compounds 5a, 5b, and 5c were found effective against E. coli (MTCC 442) and P.aeruginosa (MTCC 441) and all compounds showed moderate to excellent activity against Streptococcus aureus (MTCC 96) and Bacillius subtilis (MTCC 441). Regarding the antifungal screening, compounds 5a, 5b, and 5c exhibited excellent activity against Candida albicans MTCC 227. 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives may be used as potential lead molecules as effective antimicrobial agents.
Agarwal, Dinesh Kr.,Agarwal, Shikha,Gandhi, Divyani,Prajapat, Prakash,Sethiya, Ayushi
p. 141 - 148
(2020/02/04)

Multi-step synthesis, photophysical and physicochemical investigation of novel pyrazoline a heterocyclic D- π -A chromophore as a fluorescent chemosensor for the detection of Fe3+ metal ion
The title compound has been 2-(1-(benzo[d]thiazol-2-yl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (BTDP) synthesized by reaction of (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DMPO) with 2-Hydrazinylbenzo[d]thiazole. DMPO was synthesized by the reaction of 1-(2 hydroxyphenyl)ethan-1-one with 3,4-dimethoxybenzaldehyde. Structure of compound has been confirmed by the elemental analysis and spectroscopic techniques (FT-IR, 1H NMR and 13C NMR). Photophysical properties of the BTDP such as absorption, emission, stokes shift, transition dipole moments and fluorescence quantum yield have been studied in various solvents of different polarity and chromophore demonstrated positive solvatochromism. The chromophore undergoes micellization in two different micelles and its can be used as probe to determine the critical micelle concentration of surfactant such as CTAB and SDS. In addition, Pyrazoline derivative used as fluorescent chemosensor for metal ion selectively based on fluorometric detraction and pyrazoline displayed as on-off fluorescence chemosensor for the determination of Fe3+ ion in solution. Hildebrand, Stern-Volmer and job's plot method has described quenching behavior of chromophore with Fe3+ ion.
Khan, Salman A.
(2020/04/01)

Identification of: N -benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators
ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC50 values of 0.97, 0.37, and 0.41 ΜM, respectively. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators.
Cao, Feng,Gao, Xinfeng,Jiang, Xinhai,Li, Wenyan,Liu, Hongtao,Tian, Wenhua,Wang, Ruizhi,Wei, Liping,Xu, Chen,Xu, Yanni
p. 411 - 418
(2020/04/15)

Identification of novel GPR81 agonist lead series for target biology evaluation
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.
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)

Synthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors
Monoamine oxidases (MAO) are enzymes that catalyze the oxidative deamination of monoamines such as dopamine, noradrenaline, adrenaline, and serotonin. Recent studies have shown that numerous benzothiazole derivatives exhibit hMAO inhibitory activity in the micromolar concentration range. In this study, a novel series of benzothiazole-thiadiazole (5a-5l) was synthesized and characterized their chemical structures by 1H-NMR, 13C-NMR, and Mass spectroscopy. These compounds were evaluated as inhibitors for types A and B MAO enzymes. Compounds 5f and 5l were the most active derivatives in the series with an IC50 values of 0.107 ± 0.003 and 0.128 ± 0.004, respectively. Furthermore, cytotoxicity of compounds 5f and 5l were investigated and found as non-cytotoxic.
Acar ?evik, Ulviye,Osmaniye, Derya,Sa?lik, Begüm N.,Levent, Serkan,K. ?avu?o?lu, Betül,Karaduman, Abdullah B.,D. ?zkay, ümide,?zkay, Yusuf,Kaplancikli, Zafer A.,Turan, Gülhan
p. 2225 - 2233
(2020/03/04)

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones
We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].
Mor, Satbir,Sindhu, Suchita
p. 46 - 62
(2019/11/13)

Visible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines
A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl2. The salient features of the protocol include the utilization of atmospheric oxygen and visible light as clean, inexpensive and sustainable resources at room temperature.
Dhar S. Yadav, Lal,Krishna Pal Singh, Rana,Singh, Manjula
(2020/02/13)

Synthesis, anti-proliferative activity, SAR, and kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives
A series of novel thiazol-2-yl substituted-1-sulfonamide derivatives were synthesized from anilines. This involved the coupling of sulfonyl chlorides with thiazol amine to obtain the final compounds 7a–7j and 8a–8j. All synthesized compounds were screened for anticancer activity against MCF-7, HeLa, A-549, and Du-145 cancer cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Preliminary bioassay suggests that most of the compounds show anti-proliferation to different degrees, with doxorubicin used as positive control. The synthesized compounds show IC50 values in the range 2.74–8.17 μM in the different cell lines. The compounds 7d, 7e, 8a, 8d, and 8e were active compared to doxorubicin. The compounds having butyl and pantyl chains were more active than their lower and higher carbon chains and also their ring counterparts.
Pawar, Chandrakant D.,Chavan, Sadhana L.,Pawar, Umakant D.,Pansare, Dattatraya N.,Deshmukh, Santosh V.,Shinde, Devanand B.
p. 257 - 264
(2018/11/27)

Discovery of novel pyrimidine-based benzothiazole derivatives as potent cyclin-dependent kinase 2 inhibitors with anticancer activity
To develop novel CDK2 inhibitors as anticancer agents, a series of novel pyrimidine-based benzothiazole derivatives were designed and synthesized. Initial biological evaluation demonstrated some of target compounds displayed potent antitumor activity in vitro against five cancer cell lines. Especially, the analogue 10s exhibited approximately potency with AZD5438 toward four cells including HeLa, HCT116, PC-3, and MDA-MB-231 with IC50 values of 0.45, 0.70, 0.92, 1.80 μM, respectively. More interestingly, the most highly active compound 10s in this study also possessed promising CDK2/cyclin A2 inhibitory activities with IC50 values of 15.4 nM, which was almost 3-fold potent than positive control AZD5438, and molecular docking studies revealed that the analogue bound efficiently with the CDK2 binding site. Further studies indicated that compound 10s could induce cell cycle arrest and apoptosis in a concentration-dependent manner. These observations suggest that pyrimidine-benzothiazole hybrids represent a new class of CDK2 inhibitors and well worth further investigation aiming to generate potential anticancer agents.
Diao, Peng-Cheng,Lin, Wei-Yuan,Jian, Xie-Er,Li, Yan-Hong,You, Wen-Wei,Zhao, Pei-Liang
p. 196 - 207
(2019/07/02)

Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles
A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2–0.25 μg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).
Cheraiet, Zinelaabidine,Meliani, Saida,Nessaib, Mounir,Hessainia, Sihem,Boukhari, Abbas,Djahoudi, Abdelghani,Regainia, Zine
(2019/08/12)

Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
A new class of benzazolyl azolyl sulfamoyl acetamides was prepared from azolyl sulfamoyl acetates and benzazolyl amines in the presence of KOtBu in tetrahydrofuran. Compounds with benzothiazole-thiazole, benzimidazole-thiazole, benzothiazole-imidazole, and benzimidazole-imidazole moieties exhibited excellent antibacterial activity against Bacillus subtilis.
Rajeswari, Tankam,Rekha, Tamatam,Dinneswara Reddy, Guda,Padmaja, Adivireddy,Padmavathi, Venkatapuram
p. 2449 - 2459
(2019/08/07)

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.
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Paragraph 0013; 0018

(2019/02/13)

Nanomolar detection of 4-aminophenol using amperometric sensor based on a novel phthalocyanine
Novel cobalt (II) tetra-β-[N(2-(1,3-benzothiazole))carboxamide] phthalocyanine (CoTBTCAPc) has been synthesized for the first time. The dark green colored complex was characterized by different physicochemical and analytical techniques. Cyclic voltammetric studies revealed that the synthesized complex is redox-active nature. The CoTBTCAPc modified glassy carbon electrode (GCE/CoTBTCAPc) showed a stagnant charge transfer behavior for the redox probe whereas, composite hybrid of CoTBTCAPc with carbon nanoparticles (CNP) coated on GCE (GCE/CNP-CoTBTCAPc) showed facile and better charge transfer compared to the bare GCE. The GCE/CoTBTCAPc and GCE/CNP-CoTBTCAPc fabricated electrodes exhibited a decrease in over potential with the increase in oxidation peak current. Electrochemical oxidation of 4-aminophenol (4-AP) at nanomolar concentration was obtained in phosphate buffer pH 7.0 electrolytic media. The modified electrodes showed linear electrochemical response in the concentration range of 40–800 nM and the detection limit (LOD) was found as 13 and 11 nM (S/N = 3) for GCE/CoTBTCAPc and GCE/CNP-CoTBTCAPc electrodes respectively. Differential pulse voltammetric (DPV) technique showed linear response for the 4-AP oxidation in the concentration range of 100–1000 nM with sensitivity of 0.0328 and 0.4179 μA nM?1 cm?2 for the phthalocyanine and CNP-phthalocyanine modified electrodes respectively. In contrast, the amperometric sensor displayed linear response in the concentration range of 100–900 nM with sensitivity values of 0.4008 and 0.8887 μA nM?1 cm?2 and LOD of 40 and 30 nM for GCE/CoTBTCAPc and GCE/CNP-CoTBTCAPc electrodes respectively. The GCE/CNP-CoTBTCAPc showed selectivity for 4-AP even in the presence of interfering organic and inorganic species. This stable and simple sensor offers an opportunity for the electrochemical sensing of 4-aminophenol in real sample analysis like 4-AP in paracetamol tablets.
Nemakal, Manjunatha,Aralekallu, Shambhulinga,Mohammed, Imadadulla,Pari, Malathesh,Venugopala Reddy,Sannegowda, Lokesh Koodlur
p. 342 - 353
(2019/06/25)

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers
Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.
Chen, Ge,Niu, Chunyi,Yi, Jianhua,Sun, Lin,Cao, Hengyi,Fang, Yanjia,Jin, Taijie,Li, Ying,Lou, Chunli,Kang, Jingwu,Wei, Wanguo,Zhu, Jidong
(2019/04/01)

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers
Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.
Chen, Ge,Niu, Chunyi,Yi, Jianhua,Sun, Lin,Cao, Hengyi,Fang, Yanjia,Jin, Taijie,Li, Ying,Lou, Chunli,Kang, Jingwu,Wei, Wanguo,Zhu, Jidong
p. 3107 - 3121
(2019/04/01)

Utility of 3-(thiophen-2-yl)prop-2-enoyl isothiocyanate in heterocyclic synthesis
Convenient syntheses of quinazoline, benzothiazole, thiadiazole, imidazole, and thiourea derivatives starting from 3-(thiophen-2-yl)prop-2-enoyl isothiocyanate are described. The structures of the synthesized compounds are confirmed from their microanalytical and spectral data. Some of the products are examined for their antibacterial activity against Gram-positive and Gram-negative bacteria and fungi.
El-Sayed, Amira A,Atta-Allah, Saad R,Hemdan, Magdy M
p. 307 - 312
(2019/07/19)

Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
p. 8411 - 8422
(2019/05/17)

Convenient and efficient synthesis of novel 11: H -benzo[5,6][1,4]thiazino[3,4- a] isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1 H -indene-1,3(2 H)-diones
An unprecedented formation of 11H-benzo[5,6][1,4]thiazino[3,4-a]isoindol-11-ones through a one-step reaction of differently substituted 2-aminobenzenethiols and 2-bromo-(2/3-substitutedphenyl)-1H-indene-1,3(2H)-diones in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramolecular cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones were established by FTIR, 1H NMR, 13C NMR, HRMS, and X-ray crystallographic analysis. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.
Mor, Satbir,Sindhu, Suchita
p. 12784 - 12792
(2019/05/10)

Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury
Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll-like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases.
Chen, Lingfeng,Chen, Hongjin,Chen, Pengqin,Zhang, Wenxin,Wu, Chao,Sun, Chuchu,Luo, Wu,Zheng, Lulu,Liu, Zhiguo,Liang, Guang
p. 22 - 38
(2018/10/23)

Synthesis and antimicrobial activity of benzazolyl azolyl urea derivatives
A new class of benzazolyl azolyl urea derivatives were prepared by the reaction of methyl benzazoyl carbamates with azolyl amines in the presence of mild base potassium tert-butoxide. The presence of electron withdrawing substituents on the aromatic ring enhanced the activity. Nitro substituted benzothiazolyl thiazolyl urea, benzothiazolyl imidazolyl urea and benzimidazolyl thiazolyl urea exhibited potential antibacterial activity against Bacillus subtilis. The compound benzothiazolyl imidazolyl urea and nitro substituted benzimidazolyl imidazolyl urea showed potential antifungal activity against Aspergillus niger.
Narendra babu, Kayathi,Nagarjuna, Ummadi,Reddy, Guda Dinneswara,Padmaja, Adivireddy,Padmavathi, Venkatapuram
(2019/08/20)

[...] aromatic amines acetylcholine esterase inhibitor synthesis and use (by machine translation)
The present invention provides a formula for the (I) or (II) [...] aromatic amines of the acetylcholine esterase inhibitor and its pharmaceutically acceptable salt or a stereoisomer thereof, a process for their preparation and its in the preparation of acetylcholine esterase inhibitors and treatment of Alzheimer's disease and/or myasthenic application of the medicament, type definition of each group in the specification. The invention of aromatic amine derivatives as [...] of acetylcholine esterase inhibitors with micromolar level to nanomolar inhibiting activity, has further developed into an anti-Alzheimer's disease possibility of drug. (by machine translation)
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Paragraph 0098; 0100

(2018/10/19)

Phthaloyl Dichloride–DMF Mediated Synthesis of Benzothiazole-based 4-Formylpyrazole Derivatives: Studies on Their Antimicrobial and Antioxidant Activities
Benzothiazole-based pyrazole derivatives prepared by a molecular hybridization approach with an aim to influence the biological activity significantly. Efficient conversion of hydrazones 3a–k derived from their corresponding methyl ketones to 4-formylpyrazoles 4a–k was carried out at 60°C in dioxane, using the Vilsmeier–Haack reagent isolated from phthaloyl dichloride and N,N-dimethylformamide. The newly synthesized compounds 4a–k and hydrazones 3a–k were screened in vitro for their antimicrobial activities using the broth macrodilution method. The compounds 4a–k were also screened for their antioxidant activities using the DPPH radical scavenging assay. Some of the synthesized compounds showed significant antibacterial and antifungal activities as evident from their minimum inhibitory concentrations. Compound 4d showed remarkable antioxidant activity.
Bala, Renu,Kumari, Poonam,Sood, Sumit,Kumar, Vinod,Singh, Nasib,Singh, Karan
p. 2507 - 2515
(2018/09/25)

Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination
The direct C2-H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2-H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2-H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C-H imination in a sequential one-pot reaction.
Das, Ranajit,Banerjee, Mainak,Rai, Rakesh Kumar,Karri, Ramesh,Roy, Gouriprasanna
p. 4243 - 4260
(2018/06/22)

Copper-catalyzed synthesis of 2-aminophenyl benzothiazoles: A novel approach
A novel, convenient and efficient protocol for the construction of various 2-aminophenyl benzothiazoles by domino intra- and intermolecular C-N cross-coupling reactions of arylisothioureas with aryl iodides using an inexpensive, air stable and readily available copper catalyst is described. The arylisothioureas were obtained from thiourea via copper promoted desulfurization followed by nucleophilic substitution. In addition, the reactivity of arylhalides and the reaction mechanism have also been studied. The protocol features operational simplicity and a broad substrate scope.
Boddapati, S. N. Murthy,Kurmarayuni, Chandra Mohan,Mutchu, Baby Ramana,Tamminana, Ramana,Bollikolla, Hari Babu
p. 6889 - 6894
(2018/10/02)

Synthesis method of organic synthesis intermediate 2-aminobenzothiazole
The invention relates to a synthesis method of an organic synthesis intermediate 2-aminobenzothiazole. The synthesis method mainly comprises: adding 3 mol aniline and a 12 L isopropanol solution to areaction container, controlling the stirring speed at 110-130 rpm, adding a 1.6 L hydrochloric acid solution and 4-5 mol 2-methylthiocyanobenzene, heating the solution to a temperature of 60-70 DEG C,controlling the stirring speed at 130-150 rpm, maintaining for 90-120 min, cooling the solution to a temperature of 40-45 DEG C, refluxing for 60-80 min, carrying out placing cooling, precipitating asolid, dissolving the solid in a cyclohexane solution, carrying out pressure reducing distillation, collecting the distillate at a temperature of 80-90 DEG C, adding a 8 L oxalic acid solution, cooling the solution to a temperature of 10-16 DEG C, crystallizing, filtering, washing the crystal by using a triethylamine solution, washing with an ethylene glycol dimethyl ether solution, dewatering with a dewatering agent, and drying at a temperature of 50-58 DEG C to obtain the finished product 2-aminobenzothiazole.
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Paragraph 0011; 0013; 0014; 0015

(2018/09/11)

Discovery of 18β-glycyrrhetinic acid conjugated aminobenzothiazole derivatives as Hsp90-Cdc37 interaction disruptors that inhibit cell migration and reverse drug resistance
A series of 18β-glycyrrhetinic acid (GA) conjugated aminobenzothiazole derivatives were designed, synthesized and evaluated for disruption activity of Hsp90-Cdc37 as well as the effects of in vitro cell migration. These compounds exhibited relatively good disruption activity against Hsp90-Cdc37 with IC50 values in low micromolar range. A docking study of the most active compound 11g revealed key interactions between 11g and Hsp90-Cdc37 complex in which the benzothiazole moiety and the amine chain group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU and showed potent suppression activity against drug-resistant cancer cells. In particular, compound 11 g appeared to be the most potent compound against the A549 cell line, at least partly, by inhibition of the activity of Hsp90 and apoptosis induction. The treatment of A549 cells with compound 11g resulted in inhibition of in vitro cell migration through wound healing assay and S phase of cell cycle arrested. In addition, 11g-induced apoptosis was significantly facilitated in A549 cells. Thus, we conclude that GA aminobenzothiazole derivatives may be the potential Hsp90-Cdc37 disruptors with the ability to suppress cells migration and reversed drug-resistant.
Jin, Le,Huang, Rizhen,Huang, Xiaochao,Zhang, Bin,Ji, Min,Wang, Hengshan
p. 1759 - 1775
(2018/03/01)

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0098; 0140; 0141; 0220

(2018/03/25)

Synthesis and molecular docking of new roflumilast analogues as preferential-selective potent PDE-4B inhibitors with improved pharmacokinetic profile
In the present work, we designed and synthesized new roflumilast analogues with preferential-selective PDE-4B inhibition activity and improved pharmacokinetic properties. The unsubstituted benzo[d]thiazol-2-yl and -6-yl benzamide derivatives (4a and 6a) showed both good potency and preferential selectivity for PDE-4B. More remarkably, 6c revealed 6 times preferential PDE-4B/4D selectivity with a significant increase of in vitro cAMP and good % inhibition of TNF-α concentration. In addition, the in vitro pharmacokinetics of 6c showed good metabolic stability with in vitro CLint (5.67 mL/min/kg) and moderate % plasma protein binding (53.71%). This was reflected onto increased in vivo exposure with a half-life greater than roflumilast by 3 folds (21 h) and a Cmax value of 113.958 ng/mL. Molecular docking attributed its good activity to its key binding interactions in PDE-4B active site with additional hydrogen bonding with amino acids lining the metal pocket. Summing up, 6c can be considered as suitable candidate for further investigation for the treatment of COPD.
Moussa, Bahia A.,El-Zaher, Asmaa A.,El-Ashrey, Mohamed K.,Fouad, Marwa A.
p. 477 - 486
(2018/02/28)

Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(Substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one derivatives as antimicrobial agents
Objective: A new series 2-phenyl-3-(substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one was prepared by the fusion method by reacting 2-phenyl benzoxazine with 2-hydrazino benzothiazole and it was evaluated for their antimicrobial activity against gram positive, gram negative bacteria and fungi. Methods: Titled compounds were synthesized by fusion reactions. These compounds were evaluated by in vitro antibacterial and antifungal activity using the minimum inhibitory concentration and zone of inhibition methods. The synthesized compounds were characterized with the help of infrared, NMR and mass spectral studies. The benzothiazole moiety and the quinazoline ring have previously shown DNA gyrase inhibition and target related antibacterial activity. Thus, molecular docking studies of synthesized compounds were carried out (PDB: 3G75) to study the possible interaction of compounds with the target. The batch grid docking was performed to determine the probable. Results: These compounds showed significant activity against gram positive and gram negative bacteria as well against the fungi. The compound A5 was found to be active against B. subtilis, P aeruginosa and C. albican at 12.5 μg/ml MIC. The compound A3 was found to be active against all microbial strains selected at 25 and 12.5 μg/ml MIC. Conclusion: Though the relationship between the activities shown by these compounds in, the antimicrobial study is still to be established, the docking studies conducted found to be consistent with antimicrobial results. Thus the results indicate that the designed structure can be a potential lead as an antimicrobial agent.
Pisal, Pooja,Deodhar, Meenakshi,Kale, Amol,Nigade, Ganesh,Pawar, Smita
p. 57 - 61
(2018/10/31)

Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors
A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.
Zhang,Xu,Wang,Kang
p. 3006 - 3016
(2018/02/21)

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.
Gao, Hongyin,Zhou, Zhe,Kwon, Doo-Hyun,Coombs, James,Jones, Steven,Behnke, Nicole Erin,Ess, Daniel H.,Kürti, László
p. 681 - 688
(2017/06/30)

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles
The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.
Mallikarjuna Reddy,Lavanya,Lakshmi Teja,Padmaja,Padmavathi
p. 2755 - 2766
(2017/09/26)

Design, synthesis and biological evaluation of 1,3,4-oxadiazoles as promising anti-inflammatory agents
A series of 1,3,4-oxadiazole derivatives were designed, synthesized and evaluated for radical scavenging and anti-inflammatory properties. Molecular docking simulation studies onto the proteins cyclooxygenase-1 (PDB: 1CQE) and cyclooxygenase-2 (PDB: 3LN1) to visualize the probable binding affinity towards anti-inflammatory importance and in silico studies, towards their appreciable ADME & probable toxicity property were screened. The best-ranked molecules; N-((5-substituted-1,3, 4-oxadiazol-2-yl)methyl) benzo[d]thiazol-2-amine (5a–5j) were synthesized from 2-(benzo[d]thiazol-2-ylamino)acetohydrazide (4) on reaction with aryl/heteroaryl/aliphatic carboxylic acid derivatives via acid catalyzed dehydrative cyclization. N-((5-mercapto-1,3,4-oxadiazol-2-yl)methyl) benzo[d]thiazol-2-amine (5k) was synthesized by base catalyzed condensation of hydrazide derivative 4 and with carbon disulfide. The newly synthesized compounds were characterized and established on the basis of elemental analysis, IR, 1H NMR, 13C NMR and mass studies. The 1,3,4-oxadiazoles were evaluated for in vitro antioxidant property by 2,2′-diphenyl-1-picryl hydrazyl radical scavenging assay method and in vivo anti-inflammatory activity by carrageenan induced paw edema method. The radical scavenging activity indicated that the 1,3,4-oxadiazoles at 25 μM test concentration exhibited significant radical scavenging property ranging from 32.0 to 87.3 % in comparison to 76.0 % radical scavenging activity obtained for the reference drug, ascorbic acid. The results of the in vivo anti-inflammatory activity highlighted that the 1,3,4-oxadiazoles at 25 mg Kg?1 test dose exhibited significant edema inhibition with a mean value ranging from 23.6 to 82.3 % in comparison to 48.3 % edema inhibition obtained for the reference drug, indomethacin. The compound 5h with mean edema inhibition value of 82.3 % and potent among the series was further evaluated for in vitro COX inhibition and was found to more selective towards COX-2. The acute ulcerogenic evaluation of compound 5h indicated it to be safe at the dose of 50 mg Kg?1.
Iyer, Vishwanathan Balasubramanya,Gurupadayya, Bannimath,Koganti, Venkata Sairam,Inturi, Bharthkumar,Chandan, Ravandur Shivanna
p. 190 - 204
(2017/01/12)

Regioselective Synthesis, Antimicrobial Evaluation and QSAR Studies of Some 3-Aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones
A series of seventeen 3-aryl-1-heteroarylindeno[1,2-c]pyrazol-4(1H)-ones (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) has been synthesized and characterized by spectral (IR, 1H NMR, and mass), X-ray crystallography and analytical results. All the indenopyrazoles (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k, 4l, 4m, 4n, 4o, 4p, 4q) were tested for their in vitro antimicrobial activity against two Gram-positive bacteria viz. Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443), two Gram-negative bacteria, viz. Escherichia coli (MTCC 42) and Pseudomonas aeruginosa (MTCC 741) and two fungi, viz. Candida albicans (MTCC 183) and Aspergillus niger (MTCC 282) using ceftriaxone and fluconazole as standard references against bacterial and fungal strains, respectively. Among the synthesized derivatives, 4f against B. subtilis and S. aureus, 4e against E. coli, 4g and 4j against P. aeruginosa, 4k and 4l against C. albicans, and 4k against A. niger were found to exhibit appreciable antimicrobial activities. However, 4g (minimum inhibitory concentration, 0.0036 μmol/mL) was found to be more potent than the reference, that is, fluconazole (minimum inhibitory concentration, 0.0050 μmol/mL) against A. niger. Moreover, both antibacterial and antifungal activities were found to be prolific. The radial distribution function parameters were found to be important for description of activities against the modeled strains in quantitative structure–activity relationship studies.
Mor, Satbir,Mohil, Rajni,Nagoria, Savita,Kumar, Ashwani,Lal, Kashmiri,Kumar, Devinder,Singh, Virender
p. 1327 - 1341
(2017/03/27)

Synthesis of sulfur heterocycles via domino metal-mediated reactions
Two methodologies to access S-heterocycles and mixed N,S-heterocycles via metal-mediated domino reactions are described. One involves a cyclocarbopalladation/cross-coupling domino process and leads to benzene-fused five- or six-membered sulfur heterocycles with a stereo defined tetrasubstituted exocyclic double bond. The other consists in a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide, and an electrophile to access N-substituted 2-amino benzothiazoles. Preliminary results in the use of the second method to access N-substituted 2-imino benzothiazoles are also reported.
Castanheiro, Thomas,Suffert, Jean,Donnard, Morgan,Gulea, Mihaela
p. 162 - 165
(2017/01/22)

Benzothiazole analogues: Synthesis, characterization, MO calculations with PM6 and DFT, in silico studies and in vitro antimalarial as DHFR inhibitors and antimicrobial activities
Benzothiazole analogues are of interest due to their potential activity against malarial and microbial infections. In search of suitable antimicrobial and antimalarial agents, we report here the synthesis, characterization and biological activities of benzothiazole analogues (J 1-J 10). The molecules were characterized by IR, Mass, 1H NMR, 13C NMR and elemental analysis. The in vitro antimicrobial activity was investigated against pathogenic strains; the results were explained with the help of DFT and PM6 molecular orbital calculations. In vitro cytotoxicity and genotoxicity of the molecules were studied against S. pombe cells. In vitro antimalarial activity was studied. The active compounds J 1, J 2, J 3, J 5 and J 6 were further evaluated for enzyme inhibition efficacy against the receptor Pf-DHFR, computational and in vitro studies were carried out to examine their candidatures as lead dihydrofolate reductase inhibitors.
Thakkar, Sampark S.,Thakor, Parth,Ray, Arabinda,Doshi, Hiren,Thakkar, Vasudev R.
p. 5396 - 5406
(2017/10/06)

Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea
In the present study, a new thiourea derivative bearing benzothiazole ligand, 1-(benzo[d]thiazol-2-yl)thiourea (btt) and its ternary metal (Cu(II), Co(II) and Ni(II)) complexes were synthesized. The structural characterization was carried out by micro analysis, IR, 1H-NMR, EPR, UV-Visible spectral analyses, molar conductance and thermal analysis studies. Spectral studies of complexes revealed that the metal complexes have distorted octahedral geometry. Molecular modelling study was performed to evaluate the recognition of target compounds at the 3MNG binding pocket. The docking results revealed that copper complex selectively binds to the crucial amino acid residues in the active site of 3MNG. The in vitro antioxidant activity of the ligand and its metal complexes was assayed by radical scavenging activity (DPPH, H2O2 and NO) and ferric reducing antioxidant power (FRAP) methods. The ligand showed moderate antioxidant activity whereas the metal complexes exhibited better antioxidant activity than that of the ligand. The results of the four methods proved that the copper complex is the most potent antioxidant among all the tested compounds.
Yapati, Harinath,Devineni, Subba Rao,Chirumamilla, Suresh,Kalluru, Seshaiah
p. 43 - 51
(2016/02/09)

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules
DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.
Rothweiler, Ulli,Stensen, Wenche,Brandsdal, Bj?rn Olav,Isaksson, Johan,Leeson, Frederick Alan,Engh, Richard Alan,Svendsen, John S. Mj?en
p. 9814 - 9824
(2016/11/19)

Synthesis and anti-inflammatory activity of some novel 2- aminobenzothiazole derivatives
A series of some new 2-aminobenzothiazole derivatives (AK 1a-1g) was synthesized with the objective for evaluation as anti-inflammatory. The purity of title compound and their derivatives have been checked by TLC and C, H and N analysis and the structure was analyzed by their spectral data. The synthesized compounds were evaluated for their anti-inflammatory activity by using carrageenan-induced rat paw edema method using Diclofenac as a standard. Bioactivity score, Molecular and pharmacokinetic properties of the synthesized compounds were calculated by online computer software programme molinspiration and Osiris property explorer.
Kumar, Arun,Shakya, Ashok K.,Siddiqui
p. 243 - 249
(2019/01/18)

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
Tezuka, Noriyuki,Shimojo, Kohei,Hirano, Keiichi,Komagawa, Shinsuke,Yoshida, Kengo,Wang, Chao,Miyamoto, Kazunori,Saito, Tatsuo,Takita, Ryo,Uchiyama, Masanobu
supporting information
p. 9166 - 9171
(2016/08/05)

(NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable Carbamates: Scope and Mechanistic Studies
Primary arylamines are an important unit broadly found in synthetic, biological, and materials science. Herein we describe the development of a (NHC)Cu system that mediates a direct C-H amidation of (hetero)arenes by using N-chlorocarbamates or their sodio derivatives as the practical amino sources. A facile stoichiometric reaction of reactive copper-aryl intermediates with the amidating reagent led us to isolate key copper arylcarbamate species with the formation of a C-N bond. The use of tBuONa base made this transformation catalytic under mild conditions. The present (NHC)Cu-catalyzed C-H amidation works efficiently and selectively on a large scale over a range of arenes including polyfluorobenzenes, azoles, and quinoline N-oxides. Deprotection of the newly installed carbamate groups such as Boc and Cbz was readily performed to afford the corresponding primary arylamines.
Xie, Weilong,Yoon, Jung Hee,Chang, Sukbok
p. 12605 - 12614
(2016/10/07)