- Photochemistry of 5-nitro-1,2-benzisothiazole derivatives: effects of substituents, solvents and excitation wavelength
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3-R-5-Nitro-1,2-benzisothiazole derivatives (1, R = substituents) in solution, undergo photochemical isomerization to produce 2-R-5-nitro-1,2-benzothiazole derivatives. Here, generalizations and limitations by the substituent, solvent, and excitation wave
- Tanikawa, Hiroharu,Ishii, Kazuhiro,Kubota, Shun,Yagai, Shiki,Kitamura, Akihide,Karatsu, Takashi
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- Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles
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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
- Zhu, Yu-Shen,Shi, Linlin,Fu, Lianrong,Chen, Xiran,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
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supporting information
p. 1497 - 1500
(2021/09/09)
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- Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
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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.
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- 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
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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
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p. 141 - 148
(2020/02/04)
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- ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR
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The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))
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Page/Page column 224; 284
(2017/06/30)
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- Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions
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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
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p. 7855 - 7868
(2016/11/25)
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- Synthesis and antimicrobial activity of new pyridine derivatives-I
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2-Amino substituted benzothiazoles 2a-l and 2-chloropyridine-3-carboxylic acid 3 were used to prepare 2-[N-(substitutedbenzothiazolyl)amino]pyridine-3- carboxylic acids (4a-l) in 2-ethoxy ethanol. Acid chlorides (5a-l) were condensed with 2-hydroxyethyl piperazine (6) and 2,3-dichloropiperazine (7) to prepare amide derivatives 2-[N-(substituted benzothiazolyl)amino]pyridin-3-yl (4-(2-hydroxyethyl)piperazin-1-yl)methanones (8a-l) and 2-[N-(substituted benzothiazolyl) amino]pyridin-3-yl(2,3- dichloropiperazine-1-yl)methanones (9a-l), respectively. The structures of new compounds have been established on the basis of elemental analysis and spectral (IR, 1H NMR, and Mass spectra) studies. The in vitro antimicrobial activity was screened for all the synthesized compounds. Variable and modest activity were observed against the investigated strains of bacteria and fungi. Springer Science+Business Media, LLC 2010.
- Patel, Navin B.,Agravat, Suresh N.,Shaikh, Faiyazalam M.
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experimental part
p. 1033 - 1041
(2012/05/04)
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- Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2, 1, b]-benzothiazole derivatives
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A novel series of substituted diaryl imidazo[2, 1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted a-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.
- Malik, Jitender K.,Noolvi, Malleshappa N.,Manvi, Fakkirappa V.,Nanjwade,Patel, Harun M.,Manjula,Rao, Mallikarjuna C.,Barve, Ashutosh
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p. 717 - 724
(2012/04/05)
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- Synthesis and preliminary in-vitro cytotoxic activity of novel substituted diaryl-imidazo [2,1,b]-benzothiazole derivatives
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A novel series of substituted diaryl imidazo[2,1-b]benzothiazole derivatives (8a-y) were synthesized by condensation reaction between 2-amino benzothiazole derivatives (3a-g) and substituted α-bromo-1, 2-(substituted) diaryl-1-ethanones (7a-i). The structures of the synthesized compounds were established by IR, 1H NMR, 13C NMR and mass spectroscopical data. The compounds (8a-y) were evaluated for their in-vitro cytotoxic activity on murine (B16F10) and human (MCF-7) cancer cells by using MTT assay. From the in vitro studies compounds 8p, 8u and 8y were found most effective with an IC50 range of 0.56-27.50 μM in MCF-7 and 2.57-36.54 μM in B16F10 cells.
- Malik, Jitender K.,Noolvi, Malleshappa N.,Manvi, Fakkirappa V.,Nanjwade,Patel, Harun M.,Manjula,Mallikarjuna Rao,Barve, Ashutosh
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p. 717 - 724
(2012/05/20)
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- Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents
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Five series of thiourea derivatives bearing benzothiazole moiety (20 compounds) were efficiently synthesized and evaluated for antimicrobial and anticancer activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bacteria. Compounds 1b, 2b, 3b, 4b and 5b exhibited the greatest antimicrobial activity. Preliminary study of the structure-activity relationship revealed that electronic factors in benzothiazole rings had a great effect on the antimicrobial activity of these compounds. In preliminary MTT cytotoxicity studies, the thiourea derivatives (2d, 5c and 5d) were found most potent. In MCF-7 and HeLa cells, the IC50 values were observed in the range of 18-26?μM and 38-46?μM, respectively.
- Saeed, Sohail,Rashid, Naghmana,Jones, Peter G.,Ali, Muhammad,Hussain, Rizwan
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experimental part
p. 1323 - 1331
(2010/05/18)
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- Synthesis and antibacterial activity of a novel series of 2,3-diaryl-substituted-imidazo(2,1-b)-benzothiazole derivatives
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Benzothiazole and imidazole compounds are extensively studied heterocyclics due to their wide spectrum of bioactivities. Among them, the imidazo(2,1-b)-benzothiazole derivatives are pharmacologically important because of their immunostimulant, anti-inflammatory, antifungal, antimicrobial, antitumor, and other activities. In the present research work, a novel series of 2,3-diaryl-substituted imidazo(2,1-b)-benzothiazoles 13a-o have been synthesized by reaction of substituted 2-aminobenzothiazoles 1-8 and an appropriately substituted a-bromo-1-(4″-substituted)-phenyl-2-(4′- substituted)-phenyl-1-ethanones 9-12 in the presence of anhydrous acetonitrile. They were characterized by physicochemical, elemental, and spectral (IR, 1H-NMR, and Mass) data. All the synthesized compounds were screened for their in-vitro antibacterial activity against Gram-positive, Gram-negative bacteria. The investigation of antibacterial screening data revealed that most of the compounds tested have demonstrated congruent activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa as compared with the standard ampicillin. Among the series, compounds 13d, 13h, and 13m exhibited excellent an antibacterial activity profile as compared with the standard. In summary, preliminary results indicate that some of the newly synthesized title compounds exhibited promising antibacterial activities and they warrant more consideration as prospective antimicrobials.
- Palkar, Mahesh,Noolvi, Malleshappa,Sankangoud, Ramappa,Maddi, Veeresh,Gadad, Andanappa,Nargund, Laxmi Venkat G.
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experimental part
p. 353 - 359
(2011/07/08)
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- Synthesis and antimicrobial studies of new pyridine derivatives
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2-(p-Acetylaminobenzenesulfonylamido)-substituted benzothiazoles were prepared from 2-amino-substituted benzothiazoles and p-acetamidobenzenesulfonyl chloride using a mixture of pyridine and Ac2O, which formed an electrophilic N-acetyl- pyridinium complex facilitating condensation to give the desired products by removal of HCl. 2-[4-(Substituted benzothiazol-2-yl) aminosulfonylanilino]pyridine-3-carboxylic acids (synthesized from 2-chloropyridine-3-carboxylic acid and the corresponding substituted 2-(p-aminobenzenesulfonylamido)benzothiazole in 2-ethoxyethanol using Cu-powder and K2CO3) were then converted to acid chlorides, which on further reaction with piperazine and 4-methoxyphenylpiperazine yielded the corresponding 2-[4-(substituted benzothiazol-2-yl)amino-sulfonyl]anilino-3- (piperazinocarbonyl) pyridine and 2-[4-(substituted benzothiazol-2-yl)amino- sulfonyl]anilino-3-[(4-methoxyphenyl)piperazin-1-yl-carbonyl]pyridine. The structures of the new compounds have been established on the basis of their elemental analyses as well as IR, 1H NMR, and mass-spectral data. All the compounds have been screened for antimicrobial activity and found to possess considerable antibacterial activity.
- Patel,Agravat
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experimental part
p. 1343 - 1353
(2010/05/02)
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- 2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors
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The present invention relates to compounds of the general formula (I) and salts and physiologically functional derivatives thereof, wherein the substituent is attached to the 5- or 6- position of the benzazole; Xindependently represents S, O, SO, SO2;Yindependently represents S, O, NR2, SO, SO2;Aindependently represents ←CO-, ←CS-, ←SO-, ←SO2-, ←CO2-, ←CONR8-, ←NR8CO-, ←NR8CONR9-, ←NR8COO-, ←NR8NR9CO-, ←NR8OCO-, ←ONR8CO-, ←NR8SO2-, where ← indicates the point of attachment to R3; and wherein R1 to R19 in formula (I) represent independently of each other a variety of different substituents comprising alkyl, aryl, aralkyl, alkylaryl, heteroaryl groups and monofunctional moieties. These compounds are useful as protein kinase inhibitors in the treatment of i.a. cancer.
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Page/Page column 25
(2008/06/13)
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- 2,5- and 2,6-disubstituted benzazole analogues useful as protein kinase inhibitors
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The present invention relates to compounds of the general formulas (I), (Ia) and (II) and salts and physiologically functional derivatives thereof, wherein the substituents -Y are attached to the 5- or 6- position of the benzazole. These compounds are useful as protein kinase inhibitors in the treatment of i.a. cancer.
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Page/Page column 25
(2008/06/13)
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- Benzazole analogues and uses thereof
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The present invention relates to N2-heteroaryl-benzazole-2,(5 or 6)-diamine derivatives and compositions thereof as protein kinase inhibitors for the treatment of e.g. cancer.
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Page/Page column 25
(2008/06/13)
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- Benzazole analogues and uses thereof
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The present invention relates to compounds of the general formulas (I), (Ia) and (II) and salts and physiologically functional derivatives thereof, wherein the substituents —Y are attached to the 5- or 6-position of the benzazole.
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Page/Page column 16
(2008/06/13)
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- Synthesis and biological evaluation of benzothiazole derivatives as potent antitumor agents
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Based on 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid[2- (cyclohexanecarbonylamino)benzothiazol-6-yl]amide (1), which shows selective cytotoxicity against tumorigenic cell lines, 2,6-dichloro-N-[2- (cyclopropanecarbonylamino)benzothiazol-6-yl]benzamide (13b) was designed and synthesized as a biologically stable derivative containing no nitro group. The highly potent derivative 13b exhibited excellent in vivo inhibitory effect on tumor growth.
- Yoshida, Masao,Hayakawa, Ichiro,Hayashi, Noriyuki,Agatsuma, Toshinori,Oda, Youko,Tanzawa, Fumie,Iwasaki, Shiho,Koyama, Kumiko,Furukawa, Hidehiko,Kurakata, Shinichi,Sugano, Yuichi
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p. 3328 - 3332
(2007/10/03)
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- AMINO BENZOTHIAZOLE COMPOUNDS WITH NOS INHIBITORY ACTIVITY
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The present invention provides novel amino benzothiazole compounds, compositions comprising these compounds and methods of using these compounds as neuroprotectants. In particular, the compounds described in the present invention are useful for treating s
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- Kinetics and mechanism of methanolysis and cyclization of 1-acyl-3-(2-halo-5-nitrophenyl)thioureas
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The kinetics of methoxide ion-catalysed solvolysis of 1-acyl-3-(2-halo-5-nitrophenyl)thioureas and cyclization of fluoro derivatives were studied in methanol at 25 deg C. The cyclization involved the substitution of fluorine by sulphur anion of thiourea and proceeded in two steps. With the acetyl derivative, the first step is methanolysis and the second step is much slower cyclization of the 2-fluoro-5-nitrophenylthiourea anion formed to give 2-amino-5-nitro-1,3-benzothiazole. With the benzoyl derivative, the first step involves parallel methanolysis of the benzoyl group and cyclization to 2-benzoylamino-5-nitro-1,3-benzothiazole. At concentrations of sodium methoxide higher than ca. 0.01 mol l-1 the rates of solvolyses of all the acyl halothioureas decreased and at concentrations higher than ca. 0.01 mol l-1 the rates of solvolyses of all the acyl halothioureas decreased and at concentrations higher than ca. 0.4 mol l-1 there was an increase in the formation of other product(s) than the product of cyclization. After the addition of 18-crown-6, the side products were not formed and the cyclization of fluoro derivatives were considerably accelerated. The slowing of the solvolytic reaction and acceleration of the cyclization reaction are most probably due to the formation of dianions.
- Sedlak, Milos,Hanusek, Jiri,Holcapek, Michal,Sterba, Vijeslav
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p. 187 - 195
(2007/10/03)
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- Process for the preparation of benzothiazoles
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Benzothiazoles of the formula STR1 in which R represents H, NH2 or R1, R1 denoting alkyl or aryl, and it being possible for the ring A to have other substituents, are obtained in a simple manner by reacting the readily acc
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- Synthesis of Some New 3-(2'-Benzothiazolyl)-4(3H)-quinazolinones as Antifungal Agents
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Five new 2-methyl-3--4(3H)-quinazolinones have been synthesized.Three of them were tested for their antifungal activity against agricultural fungi by the food poison technique and the activity was compared with that of Dithan M-45.
- Lakhan, Ram,Ral, Babban J.
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p. 501 - 502
(2007/10/02)
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