- An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry
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An improved procedure for the synthesis of meloxicam drug (methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazol-2-amine-3-carboxylate 1,1-dioxide) was described in one-step using mainly impregnated montmorillonite K10 (MK10) with ZnCl2 as a heterogeneous catalyst. This innovative method was compared to the last described procedure employed in the manufacture of this anti-inflammatory drug by means of some metrics used in a first step of the evaluation process of the environmental impact of a chemical transformation. Apart from the yield, which was 90%, atom economy, waste, environmental factor, reaction mass efficiency and stoichiometric factor were calculated as 91.6%, 8.4%, 0, 8.1% and 1%, respectively. Interpretation of these metrics was given and highlighted the fact that the strategy used in the current study may be considered as an environmental-friendly and sustainable method that fits well in the green chemistry concepts.
- Dufrénoy, Pierrick,Ghinet, Alina,Hechelski, Marie,Da?ch, Adam,Waterlot, Christophe
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- Detection of Al3 + and Zn2 + ions by 2-(5-methylthiazol-2-yliminomethyl)phenol
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Aluminium chloride catalyses hydrolysis of 2-(5-methylthiazol-2- yliminomethyl)phenol (1). This reaction can be specifically used for detection of Al3 + ions in the presence of various other ions from the characteristic emission at 446 nm (λsu
- Phukan, Nithi,Baruah, Jubaraj B.
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- Identification of KPNB1 as a Cellular Target of Aminothiazole Derivatives with Anticancer Activity
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We found that aminothiazole derivative (E)-N-(5-benzylthiazol-2-yl)-3-(furan-2-yl)acrylamide (1) has strong anticancer activity, and undertook proteomics approaches to identify the target protein of compound 1, importin β1 (KPNB1). A competitive binding assay using fluorescein-labeled 1 showed that 1 has strong binding affinity for KPNB1 (Kd: ~20 nm). Furthermore, through western blotting assays for KPNB1, KPNA2, EGFR, ErbB2, and STAT3, we confirmed that 1 has inhibitory effects on the importin pathway. KPBN1 appears to be overexpressed in several cancer cells, and siRNA-induced inhibition of KPNB1 shows significant inhibition of cancer cell proliferation, while leaving non-cancerous cells unaffected. Therefore, compound 1 is a promising new lead for the development of KPNB1-targeted anticancer agents. Fluorescein-labeled 1 could be a useful quantitative probe for the development of novel KPNB1 inhibitors.
- Kim, Yong-Hak,Ha, Siyoung,Kim, Jungwon,Ham, Seung Wook
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supporting information
p. 1406 - 1409
(2016/07/16)
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- Synthesis of functionalized thiazoles via attack of heterocyclic nucleophiles on allenyl isothiocyanates
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New examples of substituted thiazole derivatives carrying different heterocyclic ring systems at C-2 position were prepared via the reaction of several allenyl isothiocyanates with nucleophiles such as imidazoles, pyrazoles, benzimidazoles, indazole, 1,2,
- Jawabrah Al-Hourani, Baker,Banert, Klaus,Gomaa, Nermeen,Vrobel, Kai
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p. 5590 - 5597
(2008/09/21)
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- One pot synthesis using supported reagents system KSCN/SiO 2-RNH3OAc/Al2O3: Synthesis of 2-aminothiazoles and N-allylthioureas
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A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from commercially available materials in one pot by using a supported reagents system, KSCN/SiO2-RNH 3OAc/Al2O3, in which α-halo ketone reacts first KSCN/SiO2 and the product, α-thiocyanatoketone, reacts with RNH3OAc/Al2O3 to give the final product, 2-aminothiazoles, in good yield and allyl bromide reacts with KSCN/SiO 2 and the product, allyl isothiocyanate, reacts with RNH 3OAc/Al2O3 to give N-allylthiourea.
- Aoyama, Tadashi,Murata, Sumiko,Arai, Izumi,Araki, Natsumi,Takido, Toshio,Suzuki, Yoshitada,Kodomari, Mitsuo
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p. 3201 - 3213
(2007/10/03)
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- Mechanism of hydrolysis of substituted N-thiazolylcarbamate esters in OH- solutions
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Substituted secondary N-thiazolylcarbamate esters and some tertiary N-methyl, N-thiazolyl carbamate esters have been synthesised and the mechanism of the OH- catalysed hydrolyses investigated. These proved to be E1cB and BAc2 respectively, and this behaviour was compared with that of other carbamates.
- Araujo, M. Eduarda M.,Norberto, Fatima,Pamplona, Teresa,Iley, Jim
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p. 664 - 667
(2007/10/03)
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- Rearrangement reactions; 14: Synthesis of functionalized thiazoles via attack of heteroatom nucleophiles on allenyl isothiocyanates
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Treatment of allenyl isothiocyanates with sulfur-, oxygen-, nitrogen- or hydride-containing nucleophiles such as propane-2-thiol, thiophenol, hydrogen sulfide, alcohols, phenol or aqueous NaOH, NH3, primary or secondary aliphatic or aromatic amines, N,N,N′,N′-tetramethylguanidine or sodium cyanoborohydride resulted in ring closure to generate thiazoles bearing a functionality at position C-2 in most cases. Moreover, we report the first examples of aromatic miazole-2-phosphonates prepared by the same strategy using dialkyl or diphenyl phosphites as nucleophiles. Georg Thieme Verlag Stuttgart.
- Banert, Klaus,Al-Hourani, Baker Jawabrah,Groth, Stefan,Vrobel, Kai
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p. 2920 - 2926
(2007/10/03)
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- Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging
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Provided are, among other things, compounds of formula I or IA, . Also provided are methods of treatment with such compounds.
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- Method for treating glaucoma IIB
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Provided is a method of decreasing intraocular pressure or improving ocular accommodation in an animal, including a human, comprising administering an intraocular pressure decreasing amount or ocular accommodation improving amount of a compound of the formula I or IA, wherein J is oxygen, sulfur, or N—Rd.
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- SYNTHESIS AND REACTIONS OF NEW VINYL ISOTHIOCYANATES
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New vinyl isothiocyanates, which can be prepared from easily accessible thiocyanates by sigmatropic shifts, show unusually high reactivity used for the synthesis of heterocyclic sulfur compounds.
- Banert, Klaus,Groth, Stefan,Hueckstaedt, Holger,Vrobel, Kai
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p. 323 - 324
(2007/10/02)
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- One-pot Preparation of 2-Chloromethyldioxolanes and 2-Aminothiazoles from Chloromethyltrioxanes
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Thermal degradation of chloromethyltrioxanes in the presence of catalytic amount of montmorillonite clay generated α-chloroaldehydes with high purity, which were treated in situ with ethylene glycol or thiourea to afford 2-chloromethyldioxolanes and 2-aminothiazoles, respectively.The clay catalysts used were removed by filtration.
- Wakasugi, Takashi,Miyakawa, Tadashi,Suzuki, Fukuichi,Itsuno, Shinichi,Ito, Koichi
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p. 2039 - 2042
(2007/10/02)
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- Substituted 6-phenylimidazo[2,1-b]]thiazoles and thiazolines as potential cardiotonic agents
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A series of phenylimidazo[2,1-b]thiazoles and thiazolines bearing one or two methoxy groups in different positions of the phenyl ring was synthesized and tested on isolated guinea pig atria. Two compounds showed a strong positive inotropic activity.
- Andreani,Rambaldi,Bonazzi,et al.
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p. 219 - 222
(2007/10/02)
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- 1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
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Antiallergy and antiulcer agents having the formula (I), STR1 and their pharmaceutically acceptable salts, wherein R1 and R2 taken separately are each hydrogen or lower alkyl; and R1 and R2 taken together are alkylene of 3-9 carbon atoms or phenylalkylene of 9-11 carbon atoms, with the proviso that the ring so formed is between 5- and 8-membered; acids of the formula (II), STR2 wherein R1 and R2 are as defined above and R3 is hydrogen, which are useful as intermediates for compounds of the formula (I), but in many instances also possess the same useful biological activity as do formula I compounds; and intermediates of the formula II wherein R1 and R2 are defined as above, and R3 is alkyl of 1 to 4 carbon atoms, carbalkoxy of 2 to 5 carbon atoms, carbophenoxy or carbobenzoxy, are also described.
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- Antiulcer thiazol-2-ylcarbamoyl-carboxylic acids, esters and amides
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This invention encompasses orally effective antiulcer agents of the formula STR1 wherein X is hydroxy, (C1 -C5)-alkoxy, phenoxy, benzyloxy, or --NH(CH2)n Y wherein n is an integer of value 2 to 4 and Y is di-(C1 -C3)-alkylamino, 1-pyrrolidinyl, 1-piperidinyl or 4-morpholinyl; R' and R" when taken together are (C3 -C8)-alkylene, with the proviso that the ring so formed is 5- to 8-membered; R' and R" when taken separately are each independently hydrogen, (C1 -C6)-alkyl or (C5 -C6)-cycloalkyl, with the proviso that when X is other than --NH(CH2)n Y, at least one of R' and R" is other than hydrogen; the pharmaceutically acceptable cationic salts thereof when X is hydroxyl, and the pharmaceutically acceptable anionic salts thereof when X is --NH(CH2)n Y.
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