- 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.
- Li, Huan,Li, Yuxin,Li, Zhengming,Shang, Junfeng,Wang, Baolei,Zhang, Yan
-
-
- Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents
-
Anaplastic lymphoma kinase (ALK) targeted therapies have demonstrated remarkable efficacy in ALK-positive lung adenocarcinomas. Here we synthesized and evaluated sixteen new 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibitors. The optimal compound 9e exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which is better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the optimal compound 9e decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that 9e could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.
- An, Baijiao,Chan, Albert S. C.,Fan, Yangyang,Li, Wei,Li, Xingshu,Wu, Feng,Yao, Han,Zhang, Niuniu
-
supporting information
(2021/07/19)
-
- Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization
-
3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.
- Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen
-
supporting information
p. 389 - 392
(2020/03/04)
-
- 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)
-
- ANTIBIOTIC COMPOUNDS
-
The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.
- -
-
Page/Page column 116; 117
(2018/03/25)
-
- 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)
-
- 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)
-
- Synthesis and antimicrobial activity of 2,4-diaryl-2,3-dihydrobenzo[b][1,4] thiazepines
-
A new series of structurally diverse 2,3-dihydrobenzo[b][1,4]thiazepines (2,3-dihydro-1,5-benzothiazepines) with substituted phenyl groups at C(2) and C(4) have been synthesized by reaction of 3-(5-bromo-2-methoxyphenyl)-1- arylpropen-1-ones with 2-aminobenzenethiols. The structures of all the synthesized compounds were confirmed by their analytical and spectral data (IR, 1H NMR, 13C NMR). All the synthesized compounds were evaluated for antibacterial and antifungal activity against a variety of bacterial and fungal strains and interesting results were obtained. Some of the compounds had antibacterial and antifungal activity comparable to that of ciprofloxacin and fluconazole.
- Kumar, Mahendra,Sharma, Kailash,Fogla, Ankur Kumar,Sharma, Kanika,Rathore, Madhu
-
p. 2555 - 2564
(2013/07/26)
-
- Fluorescence properties of 5-(5,6-dimethoxybenzothiazol-2-yl)-2′- deoxyuridine (dbtU) and oligodeoxyribonucleotides containing d btU
-
We describe the synthesis and photophysical properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)- 2′-deoxyuridine (dbtU), which was the strongest fluorescent derivative among those prepared. The fluorescence properties of dbtU itself and ODNs containing dbtU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution. The ODNs (15mer) containing 16 combinations of 5′-XbtU-3′ and 5′-btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G btU-3′ and 5′-btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-GbtU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and btUra than that of the 5′- btUG-3′ sequence and that the HOMO is delocalized not only on btUra but also on Gua.
- Hirose, Wataru,Sato, Kousuke,Matsuda, Akira
-
p. 6206 - 6217
(2011/12/02)
-
- Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem
-
In this work, 4H-1,4-benzothiazines were synthesized by an efficient synthetic method in a single step involving heterocyclization of substituted 2-aminobenzenethiols with β-ketoester. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. The synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.
- Sharma, Praveen Kumar,Fogla, Ankur,Rathore,Kumar
-
p. 1103 - 1111
(2012/04/17)
-
- Facile synthesis of bioactive 4H-[1,4]-benzothiazines under solvent free conditions
-
An efficient method for synthesis of 4H-[1,4]-benzothiazines under solvent free conditions has been developed. The oxidative condensation of 2-aminobenzenethiols with β-diketones/β-ketoesters in presence of catalytic amount of hydrazine hydrate yields the 4H-[1,4]-benzothiazines. The reaction is accelerated by microwave irradiation under solvent free conditions in presence of an energy transfer agent DMF to get the product in high yield. The 2-aminobenzenethiazole required for the synthesis of 4H-[1,4]-benzothiazines are also obtained by a new method instead of presently used time consuming and low yielding method. The structure of the synthesized compounds has been characterized by IR, NMR, mass spectral studies and elemental analysis.
- Kalwania,Chomal,Choudhary, Savita
-
p. 5133 - 5136
(2012/06/18)
-
- NOVEL COMPOUNDS
-
The invention relates to tricyclic derivatives, and their use in treating diseases and conditions mediated by antagonism of the mGluR5 receptor, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.
- -
-
Page/Page column 44
(2011/12/14)
-
- Creating an antibacterial with in vivo efficacy: Synthesis and characterization of potent inhibitors of the bacterial cell division protein FTSZ with improved pharmaceutical properties
-
3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure-activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.
- Haydon, David J.,Bennett, James M.,Brown, David,Collins, Ian,Galbraith, Greta,Lancett, Paul,MacDonald, Rebecca,Stokes, Neil R.,Chauhan, Pramod K.,Sutariya, Jignesh K.,Nayal, Narendra,Srivastava, Anil,Beanland, Joy,Hall, Robin,Henstock, Vincent,Noula, Caterina,Rockley, Chris,Czaplewski, Lloyd
-
supporting information; experimental part
p. 3927 - 3936
(2010/09/04)
-
- Identification of a novel series of tetrahydrodibenzazocines as inhibitors of 17β-hydroxysteroid dehydrogenase type 3
-
A novel series of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) inhibitors has been identified. These inhibitors, based on a dibenzazocine core, exhibited picomolar to low nanomolar inhibition of 17β-HSD3 in cell-free enzymatic as well as in cell-based transcriptional reporter assays.
- Fink, Brian E.,Gavai, Ashvinikumar V.,Tokarski, John S.,Goyal, Bindu,Misra, Raj,Xiao, Hai-Yun,Kimball, S. David,Han, Wen-Ching,Norris, Derek,Spires, Thomas E.,You, Dan,Gottardis, Marco M.,Lorenzi, Matthew V.,Vite, Gregory D.
-
p. 1532 - 1536
(2007/10/03)
-
- Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications
-
Recent efforts to identify treatments for chronic diabetic complications have resulted in the discovery of a novel series of highly potent and selective 3-[(benzothiazol-2-yl)methyl]indole-N-alkanoic acid aldose reductase inhibitors. The lead candidate, 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat, 9) inhibits aldose reductase with an IC50 of 5 nM, while being 5400 times less active against aldehyde reductase, a related enzyme involved in the detoxification of reactive aldehydes. It lowers nerve and lens sorbitol levels with ED50's of 1.9 and 4.5 mg/kg/d po, respectively, in the 5-day STZ-induced diabetic rat model. In a 3-month diabetic intervention model (1 month of diabetes followed by 2 months of drug treatment at 5 mg/kg/d po), it normalizes polyols and reduces the motor nerve conduction velocity deficit by 59% relative to diabetic controls. It has a favorable pharmacokinetic profile (F, 82%; t1/2, 5.6 h; Vd, 0.694 L/kg) with good drug penetration in target tissues (Cmax in sciatic nerve and eye are 2.36 and 1.45 μg equiv/g, respectively, when dosed with [14C] lidorestat at 10 mg/kg po).
- Van Zandt, Michael C.,Jones, Michael L.,Gunn, David E.,Geraci, Leo S.,Jones, J. Howard,Sawicki, Diane R.,Sredy, Janet,Jacot, Jorge L.,DiCioccio, A. Thomas,Petrova, Tatiana,Mitschler, Andre,Podjarny, Alberto D.
-
p. 3141 - 3152
(2007/10/03)
-
- NOVEL ALKYLAMINO DERIVATIVES
-
Compounds represented by the following formula, such as (R,S)-1-(1-adamantyl)-2-[4-(6-chloro-2-iminobenzothiazolin-3-ylmethyl)piperidin-1-yl]ethanol, or salts thereof: X-Q-C(R1)(R2)-Z wherein R1and R2each represents hydrogen, alkyl, etc. and Z represents either of groups (a) and (b), [wherein R3represents alkyl, etc.; p is an integer of 3 to 8; R4and R5each represents hydrogen, alkyl, etc.; and B represents formula (c) (wherein R6and R7each represents hydrogen, halogeno, etc. and D represents sulfur, oxygen, etc.)].
- -
-
-
- Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives
-
A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.
- Tsuruoka, Akihiko,Kaku, Yumiko,Kakinuma, Hiroyuki,Tsukada, Itaru,Yanagisawa, Manabu,Nara, Kazumasa,Naito, Toshihiko
-
p. 623 - 630
(2007/10/03)
-
- Synthesis of some new 1,4-benzothiazines and their anti psychotic activity
-
1,4-Benzothiazines (1-28) have been synthesized by treating substituted aminothiophenols with various substituted β-diketones in the presence of piperidine in THF solution.
- Chaudhari,Shinde,Shingare
-
p. 1250 - 1256
(2007/10/03)
-
- PYRIMIDO-BENZOTHIAZINES
-
This invention relates to novel pyrimido-benzothiazine derivative compounds. The compounds of the present invention inhibit the action of the lipoxygenase enzyme and are useful in the treatment or alleviation of inflammatory diseases, allergy and cardiovascular diseases in mammals. this invention also relates to pharmaceutical compositions comprising such compounds.
- -
-
-
- Synthesis of Halogen-Substituted 1,5-Benzothiazepine Derivatives and Their Vasodilating and Hypotensive Activities
-
In an attempt to improve the effectiveness and duration of the action of diltiazem (1), a 1,5-benzothiazepine calcium channel blocker, its derivatives (2) with halogen substituents on the fused benzene ring were synthesized.These compounds were evaluated for their effects on vertebral and coronary blood flows and antihypertensive activity.The structure-activity relationships are discussed.The 8-chloro derivative ((+)-2b), the most potent compound in this series, was selected for clinical evaluation as a cerebral vasodilating and antihypertensive agent.
- Inoue, Hirozumi,Konda, Mikihiko,Hashiyama, Tomiki,Otsuka, Hisao,Takahashi, Kaoru,et al.
-
p. 675 - 687
(2007/10/02)
-
- Syntheses of 1,5-Benzothiazepines: Part III - Syntheses of 4-(p-Chlorophenyl)-2-(p-methoxyphenyl)-8-substituted-2,3-dihydro-1,5-benzothiazepines
-
4-Methoxy-4'-chlorobenzalacetophenone (IV) on reaction with 5-substituted 2-aminothiophenols (IIIa-f) in toluene gives 4-(p-chlorophenyl)-2-(p-methoxyphenyl)-8-substituted-2,3-dihydro-1,5-benzothiazepines (Va-f).Their structures have been established by IR, PMR and mass spectral data.
- Pant, Umesh C.,Gaur, B. S.,Chugh, Manju
-
p. 189 - 190
(2007/10/02)
-
- A CONVENIENT AND SINGLE STEP SYNTHESIS OF SUBSTITUTED 4H-BENZOTHIAZINES.
-
A simple one step synthesis is reported for substituted 4H-benzothiazines involving the condensation of 5-(chloro, bromo, methyl, methoxy, ethoxy)-, 4-methyl- and 3-(chloro and methoxy)-2-aminobenzenethiols with acetylacetone/ethyl acetoacetate/dibenzoylmethane in DMSO.
- Gupta, R. R.,Ojha, K. G.,Kalwania, G. S.,Kumar, M.
-
p. 1145 - 1149
(2007/10/02)
-
