cas 95-24-9, 2-Amino-6-chlorobenzothiazole

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Novel benzothiazole hydrazine carboxamide hybrid scaffolds as potential in vitro GABA AT enzyme inhibitors: Synthesis, molecular docking and antiepileptic evaluation
In the present study, a series of newer benzothiazole derivatives containing thiazolidin-4-one (5a-g) and azetidin-2-one (6a-g), were synthesized by the cyclization of benzothiazolyl arylidene hydrazine carboxamide derivatives with thioglycolic acid and chloroacetyl chloride, respectively. Results of in vivo anticonvulsant screening revealed that compounds having 2,4-dicholoro (5c and 6c) and 4-nitro substituent (5g) at the phenyl ring have promising anticonvulsant activities without any neurotoxicity. Selected compounds were also evaluated for their in vitro GABA AT inhibition. The results indicated that compound 5c (IC50 15.26 μM) exhibited excellent activity as compared to the standard drug vigabatrin (IC50 39.72 μM) suggesting the potential of these benzothiazole analogues as new anticonvulsant agents.
Jamal Gilani, Sadaf,Zaheen Hassan, Mohd.,Sarim Imam, Syed,Kala, Chandra,Prakash Dixit, Surya
p. 1825 - 1830
(2019)
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Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators
With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfide-containing amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g., A2-3, A3-3 and A6-3, not only possessed favorable lethality rate (50%–100%) against P. xylostella at a concentration of 0.1 mg/L, but also held good activities towards a variety of agricultural pests such as M. separata, C. pipiens pallen, H. armigera and O. nubilalis; the larvicidal activities of A4-1 and A6-1 towards P. xylostella were close to that of chlorantraniliprole at 0.01 mg/L. The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor (RyR) modulators. The structure–activity relationships were discussed in detail. These results provide useful information for further design and development of novel insecticides.
Zhang, Yan,Li, Yuxin,Li, Huan,Shang, Junfeng,Li, Zhengming,Wang, Baolei
supporting information
p. 501 - 507
(2021/06/15)

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
supporting information

(2021/09/09)

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)

An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O
Treatment of a variety of substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F) were well tolerated. This method provides a useful alternative to other methods that are either less efficient (requiring 3–7 fold equivalents of reagents) or utilize highly toxic and corrosive liquid Br2 as the oxidizing agent.
Dass, Reuben,Peterson, Matt A.
(2021/10/04)

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.
Akhtar, Md Jawaid,Debnath, Biplab,Grover, Gourav,Nath, Rajarshi,Pathania, Shelly,Shahar Yar, M.
(2020/12/25)

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)

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)

ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light
An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.
Hosseini-Sarvari, Mona,Hosseinpour, Zeinab,Koohgard, Mehdi,Sarvestani, Abdollah Masoudi
p. 1401 - 1407
(2020/03/26)

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)

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)

Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst
By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established.
He, Wei-Bao,Gao, Lan-Qing,Chen, Xin-Jie,Wu, Zhi-Lin,Huang, Ying,Cao, Zhong,Xu, Xin-Hua,He, Wei-Min
supporting information
p. 1895 - 1898
(2020/02/27)

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)

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)

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)

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)

Benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinines: Synthesis, Structural, and Photophysical Properties
A family of highly emissive benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinines, conjugated with the donor 4-dimethylaminophenyl group, was designed and synthesized. Their photophysical, both in solution and in the solid state, and structural properties were investigated. The influence of donor and acceptor substituents (R) in the benzothiazole unit on photophysical properties of complexes was found out. The tetrafluorobenzothiazole analogue exhibits nonbonded nuclear spin-spin coupling between fluorines from the BF2 group and α-fluorine atom at the benzene ring. Additionally, this boron complex demonstrates a comparatively high solid-state fluorescence quantum yield (φ = 0.34).
Potopnyk, Mykhaylo A.,Volyniuk, Dmytro,Ceborska, Magdalena,Cmoch, Piotr,Hladka, Iryna,Danyliv, Yan,Gra?ulevi?ius, Juozas Vidas
p. 12129 - 12142
(2018/09/25)

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)

[...] 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 0104; 0105

(2018/10/19)

TYK2 INHIBITORS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.
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Paragraph 00630; 00631

(2018/04/27)

Design, synthesis, and molecular docking study of benzothiazolotriazine derivatives for anticonvulsant potential
A series of newer benzothiazolotriazine derivatives (4a–k) was designed, synthesized, and characterized as anticonvulsant agents against the two classically used MES and scPTZ animal models. The synthesized derivatives were tested in vivo in both the animal models, followed by a neurotoxicity study by the rotarod method. Compound 4e, 8-chloro-4-(2-chlorocyclohexa-1,5-dien-1-yl)-2-((4-methoxybenzyl)thio)-10aH-benzo[4,5]thiazolo[3,2a][1,3,5]triazine was found most promising among the series in both the animal models, with no neurotoxicity. From this it may be confirmed that the presence of a methoxy (OCH3) group at the lipophilic aryl ring was showing high anticonvulsant potency. In the molecular modeling study, compound 4e (docking score = ?8.70) showed important hydrogen bond interaction with the amino acids LYS 329, SER 137, GLY 136 and π–π interactions with PHE 189 at the active site of GABA-AT. These derivatives can be further explored for the development of newer/novel anticonvulsant agents.
Firdaus, Jannat Ul,Habib, Anwar,Siddiqui, Nadeem,Alam, Ozair,Naim, Mohd. Javed,Partap, Sangh,Sahu, Meeta
(2018/12/04)

N-benzothiazole benzene sulfonamide derivative as well as preparation method and application thereof
The invention discloses an N-benzothiazole benzene sulfonamide derivative as well as a preparation method and application thereof. A family-B type-I scavenger receptor (SR-BI) plays a key role in thereverse cholesterol transport process of HDL, thereby reducing the cholesterol level in plasma, inhibiting the oxidation of LDL and reducing the blood vessel injury caused by the oxidized LDL. The invention provides a series of N-benzothiazole benzene sulfonamide derivatives capable of improving the SR-BI expression, a general formula of a chemical structure is as shown in formula (I), wherein R1independently represents-OCH3, -F, -H, -Cl or -NO2, and a substituent position of a substituent group R1 on a ring A is site 3, 4, 5 or 6; and the substituent group NHR2 is in di-, meta- or para- substitution on a ring B. The prior art does not disclose a chemical structure, a preparation method and pharmaceutical activity of the N-benzothiazole benzene sulfonamide derivatives.
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(2018/09/11)

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)

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics
A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.
Jiang, Huanfeng,Yu, Wentao,Tang, Xiaodong,Li, Jianxiao,Wu, Wanqing
p. 9312 - 9320
(2017/09/22)

Design, synthesis and QSAR studies of 2-amino benzo[d]thiazolyl substituted pyrazol-5-ones: novel class of promising antibacterial agents
Abstract: Novel analogs of 3-(4-substituted benzylideneamino)-N-(6-substituted-1,3-benzo[d]thiazol-2-yl)-4,5-dihydro-5-oxo-pyrazole-1-carboxamide (5a–s) were designed and synthesized by reacting 3-amino-N-(6-substituted-1,3-benzo[d]thiazol-2-yl)-4,5-dihydro-5-oxo-pyrazole-1-carboxamide (4a–d) with p-substituted benzaldehydes. The Infrared Spectroscopy, 1H-Nuclear Magnetic Resonance, 13C-Nuclear Magnetic Resonance, and High Resolution Mass Spectra spectral data confirmed the structures of all the novel synthesized compounds. Among the series tested, two compounds 5k and 5o displayed promising antibacterial activity especially against Staphylococcus aureus (MIC = 3.14 and 1.57 μg/mL) and Bacillus subtilis (MIC = 3.12 and 1.84 μg/mL) respectively. Further, these title compounds were also assessed for their cytotoxic activity (IC50) against mammalian Vero cell line using 3-(4,5-dimethylthiazo-2-yl)-2,5-diphenyl-tetrazolium bromide assay, indicating that the compounds exhibit antibacterial activity at non-cytotoxic concentrations. Field based three-dimensional quantitative structure–activity relationships were also discussed based on the antimicrobial screening data. Graphical Abstract: Synthesis, spectral studies, antibacterial evaluation and QSAR studies of nineteen novel Schiff bases of pyrazol-5-one derivatives derived from 2-aminobenzothiazole nucleus are described.
Palkar, Mahesh B.,Patil, Aniket,Hampannavar, Girish A.,Shaikh, Mahamadhanif S.,Patel, Harun M.,Kanhed, Ashish M.,Yadav, Mange Ram,Karpoormath, Rajshekhar V.
p. 1969 - 1987
(2017/08/03)

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 Indane-Based 1,5-Benzothiazepines Derived from 3-Phenyl-2,3-dihydro-1H-inden-1-one and Antimicrobial Studies Thereof
In the present study, a series of 20 indane-based 1,5-benzothiazepines (5a–t) has been prepared derived from 3-phenyl-2,3-dihydro-1H-inden-1-one (1). All the synthesized 1,5-benzothiazepines (5a–t) were screened for their in vitro antimicrobial activities against four bacteria [Bacillus subtilis (MTCC 441), Staphylococcus epidermidis (MTCC 6880), Escherichia coli (MTCC 1652), and Pseudomonas aeruginosa (MTCC 424)] and two fungi [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)]. Among all the tested derivatives, 5n and 5o against E.?coli displayed more inhibitory activity than that of the reference drug, ciprofloxacin, while the derivatives 5c, 5m–o, 5s, and 5t against C.?albicans, and 5d, 5e, 5n, 5o, 5s, and 5t against A.?niger were found to be more potent than the standard drug, that is, fluconazole.
Mor, Satbir,Nagoria, Savita,Sindhu, Suchita,Khatri, Mohini,Sidhu, Gurdeep,Singh, Virender
p. 3282 - 3293
(2017/10/06)

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)

Design, Synthesis, and Biological Evaluation of 4-Phenoxyquinoline Derivatives Containing Benzo[d]thiazole-2-yl Urea as c-Met Kinase Inhibitors
A series of novel 4-phenoxyquinoline derivatives containing the benzo[d]thiazole-2-yl urea moiety were synthesized and evaluated for their cytotoxicity against the HT-29, MKN-45, and H460 cell lines. The structures of the target compounds were confirmed by 1H NMR and MS spectra. Most of them showed moderate to excellent potency against the three tested cell lines. Especially, compound 23 was identified a promising agent (c-Met IC50 = 17.6 nM), showing the most potent anticancer activities with IC50 values of 0.18, 0.06, and 0.01 μM against the HT-29, MKN-45, and H460 cell lines, respectively. The docking results of 23 with the c-Met kinase model 3LQ8 showed a specific binding mode between the ligand and the target protein.
Lei, Hongrui,Hu, Gang,Wang, Yu,Han, Pei,Liu, Zijian,Zhao, Yanfang,Gong, Ping
p. 651 - 661
(2016/08/27)

Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions
Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles through the reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described. In this method, all of the 2-amino-substituted benzothiazoles were obtained in high to excellent yields and short reaction times under mild conditions. The structures of the resulting products were characterized and confirmed by melting point, FT-IR, 1H NMR and 13C NMR techniques. Graphical Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles by reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described.[Figure not available: see fulltext.]
Naeimi, Hossein,Heidarnezhad, Arash
p. 7855 - 7868
(2016/11/25)

Efficient and convenient synthesis, characterization, and antimicrobial evaluation of some new tetracyclic 1,4-benzothiazines
In the present study, 20 new tetracyclic 1,4-benzothiazines (4a-4 t) were conveniently synthesized in good yields and characterized by different spectral and physical techniques. The in vitro antimicrobial evaluation of the synthesized benzothiazine derivatives was performed by serial dilution against two Gram-positive bacteria [Bacillus subtilis (MTCC 441) and Staphylococcus epidermidis (MTCC 6880)], two Gram-negative bacteria [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)], and two fungal strains [Candida albicans (MTCC 227) and Aspergillus Niger (MTCC 8189)]. The derivatives 4 l and 4 t were found to be more potent than standard drug, i.e., fluconazole, against A. Niger and C. albicans, respectively.
Mor, Satbir,Nagoria, Savita
supporting information
p. 169 - 178
(2016/02/23)

Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives
In the present study, 7-subsituted coumarin derivatives were synthesized using various aromatic and heterocyclic amines, and evaluated in vivo for anti-inflammatory and analgesic activity, and for ulcerogenic risk. The most active compounds were evaluated in vitro for 5-lipoxygenase (5-LOX) inhibition. Docking study was performed to predict the binding affinity, and orientation at the active site of the enzyme. In vivo anti-inflammatory and analgesic activity, and in vitro 5-LOX enzyme inhibition study revealed that compound 33 and 35 are the most potent compounds in all the screening methods. In vitro kinetic study of 35 showed mixed or non-competitive type of inhibition with 5-LOX enzyme. Presence of [Formula presented]3 group in 35 and [Formula presented] in 33 at C6-position of benzothiazole ring were found very important substitutions for potent activity.
Srivastava, Pavan,Vyas, Vivek K.,Variya, Bhavesh,Patel, Palak,Qureshi, Gulamnizami,Ghate, Manjunath
supporting information
p. 130 - 138
(2016/07/11)

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists
Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.
Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Perwez,Pasha, M. A. Qadar
p. 354 - 362
(2016/10/19)

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)

Catalytic Thiourea Promoted Electrophilic Thiocyanation of Indoles and Aromatic Amines with NCS/NH4SCN
A simple and efficient protocol for the electrophilic thiocyanation of indoles and aromatic amines with thiourea/NCS/NH4SCN system has been developed. The major features of the present procedure are the mild conditions, good yields, short reaction times, and the use of inexpensive and readily available organocatalyst. Moreover, N-chlorosuccinimide (NCS) was found to be indispensable, and thiourea could greatly promote the reaction.
Wang, Cancan,Wang, Zhonghao,Wang, Liang,Chen, Qun,He, Mingyang
supporting information
p. 1081 - 1085
(2016/11/25)

New Benzo[d]thiazol-2-yl-aminoacetamides as Potential Anticonvulsants: Synthesis, Activity and Prediction of Molecular Properties
A series of N-(substituted-2-oxo-4-phenylazetidin-1-yl)-2-((6-substitutedbenzo[d]thiazol-2-yl)amino)-acetamide derivatives were synthesized using pharmacophoric features with aromatic hydrophobic aryl ring (A), NH-C=O as hydrogen bonding domain, the nitrogen atom as electron donor (D), and phenyl as distal aryl ring (C). The synthesized molecules were initially screened for anticonvulsant activity using the maximal electroshock seizure (MES) test and the subcutaneous pentylenetetrazole test in albino mice. An acute neurotoxicity study on the synthesized molecules was also carried out using the rotarod test. The results of these tests revealed that two compounds, 5b and 5q, showed promising activity with ED50 values of 15.4 and 18.6 mg/kg and protective indices of 20.7 and 34.9 in the MES test, respectively, which are found to be approximately fourfold higher than those of the standard drugs phenytoin (6.9) and carbamazepine (8.1). These molecules may act as lead of the designed scheme. The pharmacokinetic profiles of all the synthesized compounds were estimated using Molinspiration software. None of the compounds violated Lipinski's "rule of five". The possible structure-activity relationship was discussed. In conclusion, this manuscript shows that the developed model has a highly prognostic power for the further investigation of better benzothiazole derivatives for future discovery and development.
Ali, Ruhi,Siddiqui, Nadeem
p. 254 - 265
(2015/04/14)

Catalytic N-formylation for synthesis of 6-substituted-2-benzothiazolylimino-5-piperazinyl-4-thiazolidinone antimicrobial agents
A new class of piperazine-based 2-benzothiazolylimino-4-thiazolidinones has been efficiently prepared via highly accelerated N-formylation of N-isopropylpiperazine by the use of a mild heterogeneous catalyst, sulfated tungstate. Heterocyclization of N-(benzo[d]thiazol-2-yl)-2-chloroacetamides (3a-j) by use of NH4SCN in ethanol under reflux efficiently furnished the intermediates 2-benzothiazolyliminothiazolidin-4-ones (4a-j). These were treated with 4-isopropylpiperazine-1-carbaldehyde (2) to prepare the final products 5a-j. The structures of the new derivatives were confirmed by elemental analysis and use of spectroscopic data (FTIR and 1H NMR). Their pharmacological potential as promising antimicrobial agents was determined in vitro against bacteria and a fungus; the lowest minimum inhibitory concentrations (MIC) observed were in the range 4-8 μg/mL.
Patel, Rahul V.,Park, Se Won
p. 5599 - 5609
(2015/07/08)

Chrysin-benzothiazole conjugates as antioxidant and anticancer agents
7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH and ABTS+ scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
Mistry, Bhupendra M.,Patel, Rahul V.,Keum, Young-Soo,Kim, Doo Hwan
supporting information
p. 5561 - 5565
(2015/11/17)

Synthesis of bioactive substituted pyrazolylbenzothiazinones
Abstract Pyrazolylbenzothiazinones have been synthesized in good yields by the reaction of 2-hydrazinocarbonymethyl-3,4-dihydro-2H-1,4-benzothiazin-3-ones with β-diketone in the presence of ethanol. The structures of synthesized pyrazolylbenzothiazinones were confirmed on the basis of their analytical and spectral data. The antimicrobial activities of the synthesized compounds have also been included.
Sharma, Praveen Kumar,Kumar
p. 6141 - 6148
(2015/08/18)

Access to a new class of biologically active quinoline based 1,2,4-triazoles
As an aspect of our ongoing research in search of new antimicrobial armamentarium, a series of 1,2,4-triazol-3-ylthio-acetamides was constructed and in vitro analyzed for their antimicrobial activity against several bacteria and fungi. Aiming to establish an increased potency, the bioassay results were matched to those of 1,3,4-oxadiazoles, utilized previously. Remarkably, 1,2,4-triazoles were found to possess a good spectrum of antifungal potency, which eventually suggested the azole template as an essential pharmacophore to diversify the biological occupations of the attendant molecules. However, it was noticed that the potency of final analogs against each strain placed reliance on the type of substituent present on benzothiazole ring. The structures of final compounds were confirmed with the aid of IR, 1H NMR, 13C NMR spectroscopy and CHN analysis.
Patel, Rahul V.,Park, Se Won
p. 24 - 30
(2013/12/04)

A facile and efficient synthesis of 2-(5-(4-substitutedphenyl)-4, 5-dihydro-3-phenylpyrazol-1-yl)-6-substitutedbenzothiazoles and their biological studies
A series of new 1-substituted 3, 5-diarylpyrazolines (10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25) were synthesized in good yield by both conventional and microwave-assisted synthesis from α, β- unsaturated ketones (6, 7, 8, 9) in n-butanol and benzothiazole hydrazines (2, 3, 4, 5). All the new compounds were characterized by IR, NMR, and mass spectral data. The synthesized compounds (10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25) were evaluated for antibacterial and anthelmintic activities. The compounds showed potent anthelmintic activity against earthworm species (Eudrilus eugeniae) and moderate antibacterial activity against bacterial strains such as Gram positive bacteria, Enterococcus faecalis, Staphylococcus aureus, and Bacillus subtilis, and Gram negative bacteria, Escherichia coli and Proteus mirabilis.
Munirajasekhar,Himaja,Mali, Sunil V.
p. 459 - 465
(2014/04/17)

Different heterocycles functionalized s-triazine analogues: Design, synthesis and in vitro antimicrobial, antituberculosis, and anti-HIV assessment
Some new quinolone condensed s-triazine derivatives endowed with different heterocycles and 4-aminobenzonitrile moiety has been synthesized and examined for their bioactivities against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, and Shigella flexneri), two fungi (Aspergillus niger, Candida albicans) by using agar streak dilution method, and Mycobacterium tuberculosis H37Rv by using Lowenstein and Jensen MIC method. Upon preliminary biological screening, it was observed that the majority of the compounds were found to possess a significant broad spectrum antimicrobial (MICs: 6.25-25 μg/mL) and antitubercular (MIC: 12.5 μg/mL) potential. Hence, anti-HIV activity against two types of HIV viral strains [HIV-1 (IIIB) and HIV-2 (ROD)] has been carried out using the MTT assay. From this bioassay, we have identified some potent inhibitors acting as anti-HIV-1 agents (IC50: 4.45g/mL) with promising therapeutic index of 16 for analogue 7 h. The structural assignments of the new products were carried out on the basis of IR, 1HNMR, 13CNMR spectroscopy, and elemental analysis.
Patel, Paresh K.,Patel, Rahul V.,Mahajan, Dharmesh H.,Parikh, Parimal A.,Mehta, Girish N.,Pannecouque, Christophe,De Clercq, Erik,Chikhalia, Kishor H.
p. 1641 - 1658
(2015/01/09)

In vitro biological investigations of novel piperazine based heterocycles
Eleven N.phenyl- and 11 N.benzothiazolyl-2-(4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)acetamides have been synthesised by a simple and efficient method. The 22 novel compounds were tested for their in vitro biological efficacy against two Grampositive bacteria, three Gram-negative bacteria, two fungi and Mycobacterium tuberculosis H37Rv. The bioassay results revealed that the majority of the N.benzothiazole-substituted piperazine derivatives exhibited moderate to good bioefficacies with encouraging MICs. The influence of the presence or absence of various electron-withdrawing or -donating functional groups on the aryl acetamide moiety on the different bioassay results is discussed.
Chhatriwala, Nirmal M.,Patel, Amit B.,Patel, Rahul V.,Kumari, Premlata
p. 611 - 616
(2015/02/02)

Synthesis and spectral properties of some azo disperse dyes containing a benzothiazole moiety
A known method was employed for the preparation of four substituted benzothiazole amines I-IV in moderate yields. These heterocyclic amines were diazotized with nitorsyl sulfuric acid and subsequently coupled with N,N-diethyl aniline and N-phenyl-2, 2′-iminodiethanol to afford heteroarylazo amine dyes 1-8 in satisfactory yields. These dyes were characterized by UV-Visible, FT-IR, 1H NMR, and elemental analysis techniques. The solvatochromism behavior of the azo compounds is investigated by studying their spectra in pure and mixed organic solvents of different characteristics. The color of the dyes is discussed with respect to the nature of the heterocyclic ring and substituent present therein. In addition, effects of acid and base on the visible absorption maxima of the dyes are also reported.
Moradi Rufchahi,Yousefi, Hessamoddin,Mohammadinia, Mojgan
p. 173 - 177
(2013/11/19)

Synthesis and biological evaluation of novel benzothiazole clubbed fluoroquinolone derivatives
In the present investigation, synthesis and anti-bacterial, analgesic and anthelmintic evaluation of a novel series of fluoroquinolone derivatives clubbed with benzothiazole moeity has been described. The synthesized compounds were characterised by spectral analysis (IR and H NMR). Preliminary results indicated that the most of the synthesized compounds demonstrated good activities against gram negative and gram positive bacterial strains. Compounds 5a, 5b, 5f and 5k demonstrated potent anti-bacterial activities. Compound 5a exhibited most potent anti-bacterial activity with MIC values of 04, 03, 08 and 15 μg/ mL against B. subtilis, S. aureus, E. coli and P. aeruginosa. Analogs 5a, 5c, 5g and 5h showed promising anthelmintic activity against Eisemia foetida in a low concentration as compared to standard drug piperazine citrate with mean paralysis time ranging 22.60 ± 2.46 to 31.60 ± 3.07 min. All synthesized compounds depicted good in vivo analgesic activity with compound 5a exhibiting the most potent activity of 55.19% inhibition of writhing in comparison to the standard drug.
Sharma, Prabodh Chander,Kumar, Ravinder,Chaudhary, Monika,Sharma, Archana,Rajak, Harish
p. 1 - 10
(2013/05/08)

Design, synthesis and anticonvulsant evaluation of N-(benzo[d]thiazol-2- ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)-carbothioamide derivatives: A hybrid pharmacophore approach
Novel N-(benzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)- carbothioamide derivatives were synthesized and evaluation of their anticonvulsant effects was done using various models of experimental epilepsy. Initial anticonvulsant activities of the compounds were investigated using intraperitoneal (i.p.) maximal electroshock shock (MES), subcutaneous pentylenetetrazole (scPTZ) seizure models in mice. The quantitative assessment after oral administration in rats showed that the most active was 2-methyl-4-oxo-N-(6-(trifluoromethoxy)benzo[d]thiazol-2-ylcarbamoyl) quinazoline-3(4H)-carbothioamide (SA 24) with ED50 values of 82.5 μmol/kg (MES) and 510.5 μmol/kg (scPTZ). This molecule was more potent than phenytoin and ethosuximide which were used as reference antiepileptic drugs. To explain the possible mechanism for anticonvulsant action, some of the selected active compounds were subjected to GABA (γ-amino butyric acid) assay and AMPA ((S)-2-amino-3-(3-hydroxyl-5-methyl-4-isoxazolyl) propionic acid) induced seizure test.
Malik, Sachin,Bahare, Radhe Shyam,Khan, Suroor Ahmad
supporting information
p. 1 - 13
(2013/10/01)

Design of benzothiazole-1,3,4-thiadiazole conjugates: Synthesis and anticonvulsant evaluation
Various 2-[(6-substituted-1,3-benzothiazol-2-yl)amino]-N-[5-substituted- phenyl-1,3,4-thiadiazol-2-yl]acetamides were synthesized with a prospective exploration of "lead hopping", using pharmacophoric elements for in vivo anticonvulsant activity. This yielded three potent candidates (5i, 5t, and 5u) in the preliminary screening employing the maximal electroshock seizure (MES) and the subcutaneous pentylenetetrazole (scPTZ) test, showing minimal neurotoxicity. Their quantitative study indicated an increase of nearly 2-10 times for the MES test and 7- to 67-fold for the scPTZ test in the protective index, the keystone in drug discovery for anticonvulsant activity. Various 2-[(6-substituted-1,3-benzothiazol-2-yl)amino]-N-[5-substituted-phenyl-1,3, 4-thiadiazol-2-yl]acetamides were synthesized with a prospective exploration of "lead hopping", using pharmacophoric elements for in vivo anticonvulsant activity. Three potent candidates (5i, 5t, and 5u) with minimal neurotoxicity were identified in the MES and scPTZ tests.
Siddiqui, Nadeem,Ahuja, Priya,Malik, Sachin,Arya, Satish K.
p. 819 - 831
(2013/12/04)

Novel 2-(2-benzylidenehydrazinyl)benzo[d]thiazole as potential antitubercular agents
Molecular hybridization approach was used to synthesize substituted 2-(2-(4-aryl oxy benzylidene) hydrazinyl)benzo thiazole derivatives with 2-hydrazinobenzothiazole and 4-(alicycli/aryl/biaryl/heteroaryl oxy)benzaldehyde as new anti-TB agents. The synthesized compounds, when tested against H37Rv strains of Mtb using Resazurin Microtitre Assay (REMA) method, showed promising activity (MIC 1.35-36.50μg/mL). 6-chloro-2-(2-(4- (pyridin-4-yloxy) benzylidene) hydrazinyl) benzo[d]thiazole (10v) gave MIC of 1.35 μg/mL. Thus making it, a potential lead could be developed for further antitubercular studies.
Bairwa, Vinod Kumar,Telvekar, Vikas N.
p. 244 - 247
(2013/07/28)

New quinolinyl-1,3,4-oxadiazoles: Synthesis, in vitro antibacterial, antifungal and antituberculosis studies
In order to generate hybrid antimicrobial remedies with novel mode of action, two series of quinoline based 1,3,4-oxadiazole derivatives condensed with N-aryl/benzothiazolyl acetamides were synthesized and the MIC values of the compounds towards eight reference bacterial strains (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), four fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and Mycobacterium tuberculosis H37Rv were assayed in vitro. Quinoline-6-carboxlic acid was treated with thionyl chloride in refluxing methanol to obtain the corresponding ester derivative to be hydrazinolyzed by 99% hydrazine hydrate in ethanol to produce carbohydrazide intermediate. The carbohydrazide precursor underwent cyclization by carbon disulfide and ethanolic KOH to construct 5-quinolinyl-6-yl-1,3,4- oxadiazol-2-thiol. Substituted 2-chloro-N-phenyl(benzothiazolyl)aceta-mide derivatives were then condensed to 1,3,4-oxadiazole nucleus via sulphur linkage to yield the desired products. Target products bearing N-benzothiazolyl-2- chloroacetamides displayed good inhibitory potential. The biological screening identified that many final analogues exhibited a significant inhibition of the growth of microorganisms at 3.12-25 μg/mL of MIC, which were comparable to control drugs. The influence of the presence of various functional groups to the phenyl/benzothiazolyl ring on activity profiles was investigated. The proposed structures of the newly prepared products were confirmed with the aid of IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. These results may provide new insights in the design of a novel pool of bioactive templates.
Patel, Rahul V.,Kumari, Premlata,Chikhalia, Kishor H.
p. 596 - 607
(2013/07/28)