- Synthesis of novel azabicyclo derivatives containing a thiazole moiety and their biological activity against pine-wood nematodes
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To explore a new skeleton with nematicidal activity, a series of novel azabicyclo derivatives containing a thiazole moiety were designed, synthesized and evaluated for their nematicidal activities. The bioassay results against pine-wood nematodes (Bursaphelenchus xylophilus) showed that most of the title compounds displayed nematicidal activity at a concentration of 40 mg/L. Especially, the title compounds2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)oxy)-4-(4-chlorophenyl)thiazole (7e), 2-((8-methyl-8-azabicyclo[3.2.1]octan-3-yl)thio)-4-phenylthiazole (10a) and 2-((8-methyl-8-azabicyclo [3.2.1]octan-3-yl)thio)-4-(4-chlorophenyl)thiazole (10e) exhibited more than 90% mortality against Bursaphelenchus xylophilus.
- Li, Hui,Lu, Aoyun,Zhang, Yanqiu,Peng, Yanqing,Song, Gonghua
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p. 371 - 375
(2020/01/02)
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- Synthesis of 4- and 5-arylthiazolinethiones as inhibitors of indoleamine 2,3-dioxygenase
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Docking studies of 4-phenylthiazolinethione on human IDO1 suggest complexation of the heme iron by the exocyclic sulfur atom further reinforced by hydrophobic interactions of the phenyl ring within pocket A of the enzyme. On this basis, chemical modifications were proposed to increase inhibition activity. Synthetic routes had to be adapted and optimized to yield the desired substituted 4- and 5-arylthiazolinethiones. Their biological evaluation shows that 5-aryl regioisomers are systematically less potent than the corresponding 4-aryl analogs. Substitution on the phenyl ring does not significantly increase inhibition potency, except for 4-Br and 4-Cl derivatives.
- Balti, Monaem,Plas, Aurélie,Meinguet, Céline,Haufroid, Marie,Thémans, Quentin,Efrit, Mohamed Lotfi,Wouters, Johan,Lanners, Steve
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supporting information
p. 3607 - 3610
(2017/07/07)
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- 2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
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The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.
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Page/Page column 42-43
(2009/10/06)
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- Lessons of 3-alkoxy-4-(p-chlorophenyl)4,3-thiazole-2(3H)-thione chemistry learned from structural investigations
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Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3-alkoxy-4-(p-chlorophenyl)-l,3-thiazole-2(3H)-thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed
- Hartung, Jens,Daniel, Kristina,Bergstraesser, Uwe,Kempter, Irina,Schneiders, Nina,Danner, Steffen,Schmidt, Philipp,Svoboda, Ingrid,Fuess, Hartmut
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experimental part
p. 4135 - 4142
(2009/12/09)
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- Synthesis and evaluation of some substituted mercaptothiazoles and their derivatives of biological interest
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The title compounds have been synthesized from 4-(4′ -chlorophenyl)-Δ4-thiazoline-2-thione1, which in turn is synthesized by the reaction of p-chlorophenacyl bromide with ammonium dithiocarbamate. Compound 1 on treatment with N-chlor
- Pattan, Shashikant R.,Sirajunisa, Talath,Pattan, Jayashri
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p. 439 - 441
(2007/10/03)
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- A facile synthesis of thiazole-2(3H)-thiones through [hydroxy(tosyloxy) iodo]benzene
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A one-pot facile synthesis of thiazole-2(3H)-thiones (4) has been achieved by hypervalent iodine oxidation of ketones (1) using [hydroxy (tosyloxy)iodo]benzene, followed by the treatment of the reaction mixture with dithiocarbamate salts (3) The intermediate α-tosyloxy-ketones (2) have also been isolated and converted to the target compounds.
- Aggarwal, Ranjana,Pundeer, Rashmi,Kumar, Vinod,Chaudhri, Vishwas,Singh, Shiv P.,Prakash, Om
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p. 2659 - 2664
(2007/10/03)
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- Hypervalent iodine in synthesis. 48. A one-pot convenient procedure for the synthesis of 2-mercaptothiazoles by cyclocondensation of ketones with [hydroxy(tosyloxy)iodo]-benzene and ammonium dithiocarbamate
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α-Tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]-benzene (HTIB), followed by treatment with ammonium dithiocarbamate, provides a one-pot convenient procedure for the synthesis of 2-mercaptothiazoles with good yields.
- Zhang,Chen
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p. 415 - 420
(2007/10/03)
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- Hypervalent iodine in synthesis; 60: A novel method for the synthesis of 2-mercaptothiazoles by cyclocondensation of alkynyl(phenyl)iodonium salts and ammonium dithiocarbamate
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A novel method for the synthesis of 2-mercaptothiazoles is achieved by cyclocondensation of alkynyl(phenyl)iodonium salts with ammonium dithiocarbamate. A reaction mechanism is proposed.
- Zhang,Chen
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p. 358 - 360
(2007/10/03)
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- Photoreactions of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones with L-cysteine derivatives in aqueous solutions
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Photolysis of substituted N-alkoxythiazolethiones 1 in aqueous solvents furnishes alkoxyl radicals 2 which, upon stereoselective 5-exo-trig cyclization, are trapped by water soluble thiols (L-cysteine, L-cysteine ethyl ester, or the reduced form of glutathione, GSH) to afford disubstituted tetrahydrofurans 3 in synthetically useful yields and with satisfactory to excellent diastereoselectivities.
- Hartung,Kneuer,Spehar
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p. 799 - 800
(2007/10/03)
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- N-hydroxy-4-(4-chlorophenyl)thiazole-2(3H)-thione as a photochemical hydroxyl-radical source: Photochemistry and oxidative damage of DNA (strand breaks) and 2′-deoxyguanosine (8-oxodG formation)
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On irradiation of N-hydroxythiazole-2(3H)-thione 3 at 300 nm, the photoproducts disulfide 4, bisthiazole 5 and thiazole 6 are formed. During this photolysis, hydroxyl radicals are released, which have been detected by spin trapping with 5,5-dimethyl-1-pyrroline N-oxide (DMPO), coupled with electron paramagnetic resonance spectroscopy. In the presence of supercoiled pBR322 DNA, irradiation of thiazolethione 3 induces strand breaks through the photogenerated hydroxyl-radicals, as confirmed by control experiment with the hydroxyl-radical scavenger isopropanol. Singlet oxygen appears not to be involved, as attested by the lack of a D2O isotope effect. During the photoreaction of thiazolethione 3 in the presence of 2′-deoxyguanosine (dG), the latter is photooxidized (ca 10% conversion after 2 h of irradiation) to the 7,8-dihydro-8-oxo-2′-deoxyguanosine as the main oxidation product. The dG conversion levels off after complete consumption of thiazolethione 3 and is suppressed by the addition of the hydroxyl-radical scavenger 2,6-di-tert-butylcresol or DMPO. Since the photoproducts 4-6 are ineffective as sensitizers for the photooxidation of dG and DNA, the hydroxyl radicals released in the photolysis of thiazolethione 3 are the oxidizing species of DNA and dG. These results suggest that the thiazolethione 3 may serve as a novel and effective photochemical hydroxyl-radical source for photobiological studies.
- Adam, Waldemar,Hartung, Jens,Okamoto, Hideki,Saha-Moeller, Chantu R.,Spehar, Kristina
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p. 619 - 624
(2007/10/03)
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- Hypervalent iodine in organic synthesis: One pot facile syntheses of α-thiocyanatoacetophenones, 2-hydroxy-, and 2-mercapto-4-arylthiazoles using [hydroxy (tosyloxy)iodo]benzene
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Hypervalent iodine oxidation of acetophenones (1a-1e) with [hydroxy(tosyloxy)iodo]benze, followed by treatment with potassium thiocyanate offers a new facile synthesis of corresponding α-thiocyanatoacetophenones (3a-3e). Cyclization of 3a-3e, thus generated in situ, using AcOH/H2O and H2NC(S)NH2/HCl provides one pot facile syntheses of 2-hydroxy-, and 2-mercapto-4-arylthiazoles (4 and 5) respectively.
- Prakash,Saini
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p. 1455 - 1462
(2007/10/02)
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- CRYSTAL ENGINEERING THROUGH NON-BONDED CONTACTS TO SULPHUR. STRUCTURE AND SOLID STATE PHOTOREACTIVITY OF 4-(4'-CHLORO)-PHENYL-Δ-4-THIAZOLENE-2-THIONE.
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Weak but directionally specific interstack S....S and S....Cl contacts may be used to engineer the 4 Angstroem - short axis β-structure for a planar sulphur heterocycle.A representative compound is the title thione 2.Crystals of 2 are monoclinic, P21
- Nalini, Veerapaneni,Desiraju, Gautam R.
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p. 1313 - 1320
(2007/10/02)
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