Month: October 2022

Desaubry, Laurent; Wermuth, Camille G.; Boehrer, Annie; Marescaux, Christian; Bourguignon, Jean-Jacques published the artcile< Synthesis and anticonvulsant properties of BW A78U structurally-related compounds>, Application In Synthesis of 31825-95-3, the main research area is BW A78U analog anticonvulsant.

Several analogs, e.g. I, of the anticonvulsant BW A78U have been synthesized and tested for their anticonvulsant properties, providing preliminary data concerning the structural requirements for this family of drugs.

Bioorganic & Medicinal Chemistry Letters published new progress about Anticonvulsants. 31825-95-3 belongs to class thiazole, and the molecular formula is C5H6N2OS, Application In Synthesis of 31825-95-3.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Fray, M. Jonathan; Bish, Gerwyn; Fish, Paul V.; Stobie, Alan; Wakenhut, Florian; Whitlock, Gavin A. published the artcile< Structure-activity relationships of N-substituted piperazine amine reuptake inhibitors>, Safety of Thiazole-5-carboxyaldehyde, the main research area is structure piperazine derivative dual serotonin noradrenaline reuptake inhibitor.

We report the structure-activity relationships of further analogs in a series of piperazine derivatives as dual inhibitors of serotonin and noradrenaline reuptake, i.e., with addnl. substitution of the Ph rings, or their replacement by heterocycles. The enantiomers of compounds 1 and 2 were also profiled, and possessed drug-like physicochem. properties. In particular, compound (-)-2 lacked potent inhibitory activity against any of the important cytochromes P450 and high selectivity over a wide range of receptors, which is unusual for a compound that inhibits human amine transporters.

Bioorganic & Medicinal Chemistry Letters published new progress about 5-HT reuptake inhibitors. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Safety of Thiazole-5-carboxyaldehyde.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Ma, Xiaohua; Ma, Fei; Zhao, Zhenhua; Song, Naiheng; Zhang, Jianping published the artcile< Synthesis and properties of NLO chromophores with fine-tuned gradient electronic structures>, Formula: C4H3NOS, the main research area is synthesis property NLO chromophores fine tuned gradient electronic structure.

A novel series of heterocycle-based NLO chromophores based on different combinations of auxiliary donor (i.e., benzene, thiophene and pyrrole) and auxiliary acceptor (i.e., thiazole with different regiochemistries) were designed and synthesized. Due to the different electron-rich and poor nature of the auxiliary donors and acceptors, resp., the resulting NLO chromophores have systematically varied ground-state electronic structures, as evidenced by the 1H NMR, CV and UV-vis investigations. The nonlinear optical properties of the resulting NLO chromophores were studied by UV-vis spectroscopy, Hyper-Rayleigh scattering (HRS), and semi-empirical computations. All the chromophores have very large mol. hyperpolarizabilities (β1000 nm) in the range of 704-1500 × 10-30 esu (or β0, 318-768 × 10-30 esu), which showed a great sensitivity to the gradient electronic structures. Upon increasing the electron d. from benzene to thiophene and to pyrrole, substantial increases in β0 were observed; significantly larger β0 values were also observed for NLO chromophores based on “”matched”” thiazole (C2 is connected to the acceptor) than those based on “”un-matched”” thiazole (C5 is connected to the acceptor). TGA investigations showed good thermal stability for the resulting NLO chromophores. However, with the increase of electron d. of the auxiliary donor, a decrease in thermal and photochem. stability was observed It is interesting to note that NLO chromophores based on triarylamine as the donor and thiazole as the auxiliary acceptor exhibited not only high thermal stability but also very large β0 values.

Journal of Materials Chemistry published new progress about Chromophores. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Formula: C4H3NOS.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Li, Shufeng; Ruan, Zhiyang; Zhang, Hang; Xu, Haiwei published the artcile< Recent achievements of bioluminescence imaging based on firefly luciferin-luciferase system>, Electric Literature of 2591-17-5, the main research area is Bioluminescence imaging (BLI); Caged luciferins; Disease diagnosis and therapy; Firefly luciferin-luciferase system; Mutant luciferase-luciferin pairs.

Bioluminescence imaging (BLI) is a newly developed noninvasive visual approach which facilitates the understanding of a plethora of biol. processes in vitro and in vivo due to the high sensitivity, resolution and selectivity, low background signal, and the lack of external light excitation. BLI based on firefly luciferin-luciferase system has been widely used for the activity evaluation of tumor-specific enzymes, for the detection of diseases-related bioactive small mols. and metal ions, and for the diagnosis and therapy of diseases including the studies of drug transport, the research of immune response, and the evaluation of drug potency and tissue distribution. In this review, we highlight the recent achievements in luciferin derivatives with red-shifted emission spectra, mutant luciferase-luciferin pairs, and the diagnostic and therapeutic application of BLI based on firefly luciferin-luciferase system. The development and application of BLI will expand our knowledge of the occurrence and development of diseases and shed light on the diagnosis and treatment of various diseases.

European Journal of Medicinal Chemistry published new progress about 2591-17-5. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Electric Literature of 2591-17-5.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Evans, David A.; Downey, C. Wade; Shaw, Jared T.; Tedrow, Jason S. published the artcile< Magnesium Halide-Catalyzed Anti-Aldol Reactions of Chiral N-Acylthiazolidinethiones>, Category: thiazole, the main research area is acylthiazolidinethione aldehyde anti aldol condensation; aldol condensation catalyst magnesium halide; alc stereoselective preparation.

Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the anti diastereomer, e.g., I. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.

Organic Letters published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Sudhaharan, T.; Reddy, A. Ram published the artcile< Metal ion-mediated inhibition of firefly bioluminescence: a possibility via a quaternary complex>, Quality Control of 115144-35-9, the main research area is ATP luciferase luciferin metal ion complex firefly bioluminescence; Photinus bioluminescence ATP luciferase luciferin metal ion complex; conformation luciferase metal ion bioluminescence firefly.

D(-)-Luciferin, interacts with different metal ions to produce colorless soluble salts with absorption spectra broader, intense and red shifted as compared to those of the parent compound The equilibrium constants for the luciferin-metal ion system vary in the order, depository divalent transition metal ions > alkali metal ions. The equilibrium constants for the ternary complexes formed between metal ions and a mixture of luciferin and luciferase are larger than that of binary complexes but vary in the same order. Steady state fluorometric titration’s of luciferin further confirmed its complexation with metal ions. The single absorption maximum of firefly luciferase at 278 nm originating from tyrosine was split into a doublet in presence of transition metal ions. The absorption maximum at lower wavelength is attributed to the H-bond ruptured free tyrosine denatured conformation of the luciferase while the longer wavelength band to tyrosine-transition metal ion complex. Difference spectra of luciferase metal ion complex yielded change in the molar extinction coefficients from which the number of tyrosine mols. exposed to aqueous solution by the perturbant metal ions are evaluated following the Donovan model. The number of tyrosine mols. exposed to the aqueous medium as a result of conformational change in the enzyme are 4, 3, 3, 2 and 3 by Hg2+, Mn2+, Co2+, Cd2+ and Cs+, resp. The denaturation constants calculated for the luciferase-metal ion complexes vary between 0.152 and 0.570 and follow the order of Hg2+ > Cs+ > Cd2+ > Co2+ > Mn2+. Steady state fluorescence data reveal that the metal ions quench the fluorescence of enzyme by complexation with the side chain residues of the excited state tyrosine. Profound change in the UV CD spectrum of luciferin and luciferase in presence of metal ions was attributed to the conformational change in the substrate and enzyme. Thus the inhibition of luciferase activity in the firefly bioluminescence by metal ions is attributed to the quaternary complex formed between metal ion-luciferin-luciferase and ATP near or around the active site of the enzyme.

Indian Journal of Biochemistry & Biophysics published new progress about Bioluminescence. 115144-35-9 belongs to class thiazole, and the molecular formula is C11H7KN2O3S2, Quality Control of 115144-35-9.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Zhang, Dong; Gao, Di; Cai, Jinlin; Wu, Xiaoyu; Qin, Hong; Qiao, Kai; Liu, Chengkou; Fang, Zheng; Guo, Kai published the artcile< The ruthenium-catalyzed meta-selective C-H nitration of various azole ring-substituted arenes>, Product Details of C10H7NOS, the main research area is ruthenium catalyst meta selective nitration azole arene green chem.

The efficient ruthenium-catalyzed meta-selective CAr-H nitration of azole ring substituted arenes has been developed. In this work, Ru3(CO)12 was used as the catalyst, AgNO2 as the nitro source, HPcy3+·BF4- as the ligand, pivalic acid as the additive, and DCE as the solvent, and a wide spectrum of arenes bearing thiazole, pyrazolyl or removable oxazoline directing groups were tolerated in this meta-selective CAr-H nitration, affording the nitrated products in moderate to good yields. Moreover, this study reveals a gentler and environmentally friendly way to access meta-nitration arenes compared to the traditional process.

Organic & Biomolecular Chemistry published new progress about Azoles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Product Details of C10H7NOS.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Wu, Yikang; Shen, Xin; Yang, Yong-Qing; Hu, Qi; Huang, Jia-Hui published the artcile< Enantioselective Total Synthesis of (+)-Brefeldin A and 7-epi-Brefeldin A>, Category: thiazole, the main research area is asym synthesis brefeldin a epibrefeldin stereoselective aldol chiral auxiliary; chiral auxiliary oxazolidinone thiazolidinethione stereoselective aldol reaction protecting group; stereoselective reduction elimination solvent effect asym synthesis brefeldin a; intramol Mukaiyama aldol condensation stereoselective Michael asym synthesis brefeldin.

A convergent enantioselective route to brefeldin A (I) and 7-epi-BFA was developed. The key C-4/C-5 chiral centers were established by using chiral auxiliary induced intermol. asym. aldolization in the presence of TiCl4 and TMEDA. The results with the thiazolidinethione/TiCl4 mediated intermol. asym. aldolization added some new information about the scope and limitations to the existing knowledge of that type of reactions (which so far was essentially limited to the reactions with N-propionyl thiazolidinethiones). During the course a method for protecting the liable aldol hydroxyl groups by using inexpensive TBSCl in DMF with 2,6-lutidine as the base was developed to replace the otherwise unavoidable TBSOTf procedure. Due to the excessive steric hindrance, removal of the auxiliary was much more difficult than most literature cases. Cleavage of the oxazolidinone by reduction was almost impossible. The thiazolidinethione auxiliary was relatively easier to remove. However, several reactions reported for facile removal of thiazolidinethione auxiliaries in the literature still failed. Reductive removal of the thiazolidinethione auxiliary was most effectively realized with LiBH4 in di-Et ether in the presence of 1 equiv of MeOH (a modification of a literature procedure for removal of oxazolidinone auxiliaries in less hindered substrates). Apart from the auxiliary removal, oxidation of the alc. into aldehyde and the deprotection of the dithiolane protecting group were also rather difficult in the present context. A range of methods were screened before final solutions were found. The five-membered ring was constructed by employing an intramol. Mukaiyama reaction after many attempts with the intramol. aldolization under a variety of conditions failed. The rate of elimination of the alkoxyl to form the α,β-double bond of a key intermediate cyclopentenone with DBU was highly solvent dependent (very sluggish in CH2Cl2 but rather fast in MeOH). Introduction of the lower chain (which was synthesized by using a Jacobsen KHR to establish the C-15 chirality) was achieved through a Michael addition similar to the precedents in the literature. It has not been noticed before that the yield of this Michael reaction could be dramatically raised by using 3 equiv of the copper-lithium reagent. Reduction of the C-7 carbonyl was apparently more difficult than similar cases in the literature. After examination of many reagents under various conditions, it was found that the best reagent for yielding the α-isomer was (S)-2-methyl-CBS-borolidine/BH3 and that for the β-isomer was L-Selectride. The α- and β-isomers were then further elaborated into (+)-brefeldin A and 7-epi-BFA, resp. An unexpected yet very interesting solubility difference between BFA and 7-epi-BFA was also observed

Journal of Organic Chemistry published new progress about Aldol condensation, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Kadam, Shuddhodan N.; Ambhore, Ajay N.; Hebade, Madhav J.; Kamble, Rahul D.; Hese, Shrikant V.; Gaikwad, Milind V.; Gavhane, Priya D.; Dawane, Bhaskar S. published the artcile< Metal-Free One-Pot Chemoselective Thiocyanation of Imidazothiazoles and 2-Aminothiazoles with in situ Generated N-Thiocyanatosuccinimide>, Formula: C9H7N3O2S, the main research area is thiocyanoimidazothiazole thiocyanoaminothiazole preparation green chem; imidazothiazole aminothiazole metal free chemoselective thiocyanation.

A chemoselective thiocyanation of imidazothiazoles and 2-aminothiazoles with use of in situ generated N-thiocyanatosuccinimide (NTS) at room temperature is described. The protocol offers mild reaction conditions and high chemoselectivity for electrophilic substitution in imidazothiazoles over nucleophilic substitution. This method provides metal-free and easy conversion of imidazothiazoles and 2-aminothiazoles into their corresponding C-3 and C-5 thiocyanates, resp., in good to excellent yield. The present protocol also offers the effective thiocyanation of bifunctional imidazothiazoles containing aliphatic -OH and C(sp2)-H bond functionalities.

Synlett published new progress about Chemoselectivity. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Formula: C9H7N3O2S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Li, Xiaokai; Srinivasan, Sharan R.; Connarn, Jamie; Ahmad, Atta; Young, Zapporah T.; Kabza, Adam M.; Zuiderweg, Erik. R. P.; Sun, Duxin; Gestwicki, Jason E. published the artcile< Analogues of the Allosteric Heat Shock Protein 70 (Hsp70) Inhibitor, MKT-077, As Anti-Cancer Agents>, Product Details of C10H9NOS2, the main research area is benthiazolyl cationic rhodacyanine preparation allosteric Hsp70 inhibitor antitumor; Hsp90; breast cancer; mortalin; p53; proteostasis.

The rhodacyanine, MKT-077, has antiproliferative activity against cancer cell lines through its ability to inhibit members of the heat shock protein 70 (Hsp70) family of mol. chaperones. However, MKT-077 is rapidly metabolized, which limits its use as either a chem. probe or potential therapeutic. The synthesis and characterization of MKT-077 analogs designed for greater stability is reported. The most potent mols., such as I (JG-98), were at least 3-fold more active than MKT-077 against the breast cancer cell lines MDA-MB-231 and MCF-7 (EC50 values of 0.4 ± 0.03 and 0.7 ± 0.2 μM, resp.). The analogs modestly destabilized the chaperone clients, Akt1 and Raf1, and induced apoptosis in these cells. Further, the microsomal half-life of JG-98 was improved at least 7-fold (t1/2 = 37 min) compared to MKT-077 (t1/2 < 5 min). Finally, NMR titration experiments suggested that these analogs bind an allosteric site that is known to accommodate MKT-077. These studies advance MKT-077 analogs as chem. probes for studying Hsp70s roles in cancer. ACS Medicinal Chemistry Letters published new progress about Antiproliferative agents. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Product Details of C10H9NOS2.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica