Day: October 12, 2022

Su, H.; Yang, J.-H.; Lu, C.-F.; Chen, Z.-X.; Yang, G.-C. published the artcile< A study of the alkylation and acylation of N-acylthiazolidinethione>, Reference of 171877-39-7, the main research area is acylthiazolidinethione alkylation acylation.

Studying the alkylation and acylation of N-acylthiazolidinethione, the desired α-alkylated products and C-acylated products are not obtained, but rather the S-alkylated products and O-acylated products were obtained. The possible mechanism proposed shows that the deprotonation agent and electrophilic species are responsible for the stability of enolates. The enolates derived from N-acylthiazolidinethiones are decomposed in the presence of base, but they are comparatively stable in the presence of Lewis acid. When electrophilic reagent is alkyl halide, the enolate decomposition is the dominating pathway, and affords the S-alkylated products; and when electrophilic reagent is acyl chloride, the formation of a highly ordered chelated transition-state is the dominating pathway, and affords the O-acylated products.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Reference of 171877-39-7.

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

Viviani, Vadim R.; Bevilaqua, Vanessa R.; de Souza, Daniel R.; Pelentir, Gabriel F.; Kakiuchi, Michio; Hirano, Takashi published the artcile< A very bright far-red bioluminescence emitting combination based on engineered railroad worm luciferase and 6′-amino-analogs for bioimaging purposes>, Synthetic Route of 2591-17-5, the main research area is far red bioluminescence emitting luciferase amino analog bioimaging; Far-Red bioluminescence; NIR bioluminescence; bioimaging; biophotonics; luciferin amino-analogs.

Beetle luciferases produce bioluminescence (BL) colors ranging from green to red, having been extensively used for many bioanal. purposes, including bioimaging of pathogen infections and metastasis proliferation in living animal models and cell culture. For bioimaging purposes in mammalian tissues, red bioluminescence is preferred, due to the lower self-absorption of light at longer wavelengths by Hb, myoglobin and melanin. Red bioluminescence is naturally produced only by Phrixothrix hirtus railroad worm luciferase (PxRE), and by some engineered beetle luciferases. However, Far-Red (FR) and Near-IR (NIR) bioluminescence is best suited for bioimaging in mammalian tissues due to its higher penetrability. Although some FR and NIR emitting luciferin analogs have been already developed, they usually emit much lower bioluminescence activity when compared to the original luciferin-luciferases. Using site-directed mutagenesis of PxRE luciferase in combination with 6′-modified amino-luciferin analogs, we finally selected novel FR combinations displaying BL ranging from 636-655 nm. Among them, the combination of PxRE-R215K mutant with 6′-(1-pyrrolidinyl)luciferin proved to be the best combination, displaying the highest BL activity with a catalytic efficiency ~2.5 times higher than the combination with native firefly luciferin, producing the second most FR-shifted bioluminescence (650 nm), being several orders of magnitude brighter than com. AkaLumine with firefly luciferase. Such combination also showed higher thermostability, slower BL decay time and better penetrability across bacterial cell membranes, resulting in ~3 times higher in vivo BL activity in bacterial cells than with firefly luciferin. Overall, this is the brightest FR emitting combination ever reported, and is very promising for bioimaging purposes in mammalian tissues.

International Journal of Molecular Sciences published new progress about Biological imaging. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Synthetic Route of 2591-17-5.

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

Jin, Ming Yu; Zhou, Yali; Xiao, Dengmengfei; You, Yipeng; Zhen, Qianqian; Tao, Guanyu; Yu, Peiyuan; Xing, Xiangyou published the artcile< Simultaneous Kinetic Resolution and Asymmetric Induction within a Borrowing Hydrogen Cascade Mediated by a Single Catalyst>, COA of Formula: C10H7NOS, the main research area is unsaturated ketone preparation; alkoxy ketone preparation; ketone amino preparation; alc alkoxy preparation enantioselective; amino alc preparation enantioselective; racemic allylic alc borrowing hydrogen cascade ruthenium catalyst; asymmetric induction; borrowing hydrogen cascade; density functional theory; kinetic resolution; π-π interactions.

In a borrowing hydrogen cascade starting from racemic allylic alcs., one of the enantiomers could be kinetically resolved, while the other enantiomer could be purposely converted to various targeted products, including α,β-unsaturated ketones RC(O)C=CCH2R1 [R = Ph, 4-FC6H4, 2-naphthyl, etc.; R1 = (CH2)6, (CH2)7, OTBS], β-functionalized ketones R2C(O)CH2CH2R3 [R2 = 4-MeSC6H4, 4-t-BuC6H4, 4-MeOC6H4, etc.; R3 = OMe, OEt, morpholino, etc.] and γ-functionalized alcs. R4CH(OH)CH2CH2R5 [R4 = 4-ClC6H4, 4-FC6H4, 2-naphthyl, etc.; R5 = OMe, OBn, morpholino, etc.] was reported. By employing a robust Ru-catalyst, both kinetic resolution and asym. induction were achieved with remarkable levels of efficiency and enantioselectivity. D. functional theory (DFT) calculations suggested that corresponding catalyst-substrate π-π interactions were pivotal to realize the observed stereochem. diversity.

Angewandte Chemie, International Edition published new progress about Alcohols, alkoxy Role: SPN (Synthetic Preparation), PREP (Preparation). 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, COA of Formula: C10H7NOS.

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

Wang, Chenchen; Du, Wei; Zhang, Tong; Liang, Gaolin published the artcile< A Bioluminescent Probe for Simultaneously Imaging Esterase and Histone Deacetylase Activity in a Tumor>, COA of Formula: C11H8N2O3S2, the main research area is histone deacetylase esterase tumor imaging bioluminescent probe.

The monitoring of esterase (CES) and histone deacetylase (HDAC) activity in living cells has great potential for rapid diagnosis of malignant tumors. At present, using one bioluminescence (BL) probe to simultaneously detect (or image) these two enzymes’ activity in tumors has not been reported. Herein, a bioluminescence “”turn-on”” probe AcAH-Luc (6-acetamidohexanoic acid-D-luciferin) was rationally designed for simultaneously imaging CES and HDAC activity with excellent sensitivity and selectivity. AcAH-Luc was successfully applied in vitro to selectively detect CES and HDAC6, a subtype of HDAC, at a linear concentration range of 0-100 and 0-120 nM with limits of detection (LODs) of 0.495 and 1.14 nM, resp. In vivo results indicated that about 1/2 and 1/3 of the “”turn-on”” BL signal of AcAH-Luc was contributed by CES and HDAC activity in the tumors, resp. We envision that AcAH-Luc might be applied to simultaneously measure (and image) CES and HDAC activity in the clinic for assisting with the precise diagnosis of malignant tumors in the near future.

Analytical Chemistry (Washington, DC, United States) published new progress about Bioluminescence (probe). 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, COA of Formula: C11H8N2O3S2.

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

Maruyama, Takahisa; Kano, Yuko; Yamamoto, Yasuo; Kurazono, Mizuyo; Iwamatsu, Katsuyoshi; Atsumi, Kunio; Shitara, Eiki published the artcile< Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems>, Formula: C4H3NOS, the main research area is imidazo thiazolyl carbapenem preparation antibacterial SAR.

A new series of 1β-Me carbapenems, possessing a 7-substituted imidazo[5,1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus, was synthesized and evaluated for antibacterial activity. These compounds showed potent activities against Gram-pos. bacteria, in particular methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae (PRSP). They also exhibited potent activity against β-lactamase-neg. ampicillin-resistant Haemophilus influenzae (BLNAR).

Bioorganic & Medicinal Chemistry published new progress about Antibacterial agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Formula: C4H3NOS.

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

Cauquis, G.; Fahmy, H. M.; Pierre, G.; Elnagdi, M. H. published the artcile< Electrochemical oxidation of substituted thiazoles: 2-amino-4-ethoxycarbonyl-5-methylthiazole and N-ethoxycarbonyl-N'-(4-ethoxycarbonyl-5-methylthiazol-2-yl)thiourea>, Formula: C7H10N2O2S, the main research area is hydrogen bond thiazole electrochem; thiazole derivative oxidation electrochem; aminoethoxycarbonylmethylthiazole oxidation electrochem; thiourea thiazole oxidation electrochem.

The oxidation of I (R = H or CSNHCO2Et) on a rotating Pt disk electrode was examined in MeCN. The main products were azo and hydrazo dimeric compounds The stability of the hydrazo dimers and their azine tautomers is due to H-bonding. The thiazole ring was unattacked by the reactions. A mechanism for the oxidation is discussed.

Electrochimica Acta published new progress about 72054-60-5. 72054-60-5 belongs to class thiazole, and the molecular formula is C7H10N2O2S, Formula: C7H10N2O2S.

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

Liu, Gui-Chun; Dong, Zhi-Wei; Hou, Qing-Bai; He, Jin-Wu; Zhao, Ruo-Ping; Wang, Wen; Li, Xue-Yan published the artcile< Second Rhagophthalmid Luciferase Cloned from Chinese Glow-worm Menghuoius giganteus (Rhagophthalmidae: Elateroidea)>, Quality Control of 2591-17-5, the main research area is sequence luciferase mol cloning Rhagophthalmus Menghuoius.

The pH-insensitive beetle luciferases cloned from Rhagophthalmidae, Phengodidae, and Elateridae exhibit great potential application as reporter assays for monitoring gene expression. At present, however, only one luciferase has been reported from the enigmatic and predominantly Asian distributed luminous family Rhagophthalmidae. Here, we cloned the second rhagophthalmid luciferase from the Chinese glow-worm Menghuoius giganteus (Rhagophthalmidae: Elateroidea) by combining reverse transcription polymerase chain reaction (RT-PCR) with rapid amplification of complementary DNA ends (RACE). The luciferase consisted of 546 amino acids and showed high identity to that of Rhagophthalmus ohbai (90.4%). The recombinant M. giganteus luciferase was produced in vitro and exhibited significant bioluminescent activity under neutral conditions (pH 7.8), with low KM for D-luciferin (2.2μM) and ATP (53μM). Activity was highest at 10°C and inactivation occurred at 45°C. This luciferase showed pH-insensitivity and maximum emission spectrum at 560 nm. Phylogenetic analyses based on the deduced amino acids indicated a close relationship between the M. giganteus luciferase and that of R. ohbai. These results increase our understanding of rhagophthalmid luciferases and provide a new resource for the application of luciferases.

Photochemistry and Photobiology published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Quality Control of 2591-17-5.

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

El-Dash, Yara; Elzayat, Emad; Abdou, Amr M.; Hassan, Rasha A. published the artcile< Novel thienopyrimidine-aminothiazole hybrids: Design, synthesis, antimicrobial screening, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and VEGFR-2 inhibition>, Reference of 57493-24-0, the main research area is arylthiazolyl benzothienylpyrimidinylthioacetamide preparation antitumor activity VEGFR2 inhibition; structure arylthiazolyl benzothienylpyrimidinylthioacetamide antitumor activity VEGFR2 inhibition; lack antibacterial activity arylthiazolyl benzothienylpyrimidinylthioacetamide; antifungal activity arylthiazolyl benzothienylpyrimidinylthioacetamide; Aminothiazole; Anti-proliferative; Antimicrobial activity; Cell cycle arrest profile; Phosphorylated VEGFR-2, Caspase-3; Synthesis; Thienopyrimidine; VEGFR-2.

A series of novel hybrid compounds of hexahydrobenzo[4,5]thieno[2,3-d]pyrimidine with aminothiazole scaffolds I (R = H, Br, O2N; R1 = H, Cl, Br; R2 = H, Me) were synthesized. The synthesized compounds were evaluated for their cytotoxic activity against the NCI-60 human tumor cell line panel. Compounds I (R = H; R1 = Cl; R2 = H) (II), I (R = Br; R1 = ; R2 = H) (III) and I (R = R1 = R2 = H) exhibited significant antiproliferative activities at 10-5 M dose. II exhibited excellent cytotoxic activity against CNS cancer cell lines including SNB-75 and SF-295 as well as renal cancer cell line CAKI-1 when compared with sorafenib as standard anticancer drug. In addition, III showed almost comparable anticancer activity to sorafenib against SNB-75 cell line and displayed moderate activity against SF-295 and CAKI-1 cell lines in comparison to sorafenib. II inhibited the vascular endothelial growth factor receptor 2 (VEGFR-2) with IC50 of 62.48 ± 3.7 nM and decreased both total VEGFR-2 and phosphorylated VEGFR-2 in treated SNB-75 cells suggesting its ability to down regulate cell proliferation, growth, and survival.. The flow cytometric anal. showed that II displayed its cytotoxic activity through the reduction of the cellular proliferation and induction of cell cycle arrest at the G2/M phase. II clearly boosted the level of the apoptotic caspase-3. All the synthesized compounds were also screened for their antibacterial and antifungal activity against four pathogenic strains of both Gram-pos. and Gram-neg. as well as Candida albicans. III exhibited antifungal activity against Candida albicans compared to nystatin as the standard antifungal compound

Bioorganic Chemistry published new progress about Antitumor agents. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Reference of 57493-24-0.

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

Wilkinson, Isabel V. L.; Reynolds, Jessica K.; Galan, Sebastien R. G.; Vuorinen, Aini; Sills, Adam J.; Pires, Elisabete; Wynne, Graham M.; Wilson, Francis X.; Russell, Angela J. published the artcile< Characterisation of utrophin modulator SMT C1100 as a non-competitive inhibitor of firefly luciferase>, Safety of Potassium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylate, the main research area is firefly luciferase bioluminescence enzyme kinetics inhibitor duchenne muscular dystrophy; Assay interference; Bioluminescence; Duchenne muscular dystrophy; Enzyme inhibitor; Enzyme kinetics; Enzyme mechanism; Firefly luciferase; Inhibition mechanism; Photoaffinity probe.

Firefly luciferase (FLuc) is a powerful tool for mol. and cellular biol., and popular in high-throughput screening and drug discovery. However, FLuc assays have been plagued with pos. and neg. artifacts due to stabilization and inhibition by small mols. from a range of chem. classes. Here we disclose Phase II clin. compound SMT C1100 for the treatment of Duchenne muscular dystrophy as an FLuc inhibitor (KD of 0.40 ± 0.15μM). Enzyme kinetic studies using SMT C1100 and other non-competitive inhibitors including resveratrol and NFκBAI4 identified previously undescribed modes of inhibition with respect to FLuc’s luciferyl adenylate intermediate. Employing a photoaffinity strategy to identify SMT C1100’s binding site, a photolabeled SMT C1100 probe instead underwent FLuc-dependent photooxidation Our findings support novel binding sites on FLuc for non-competitive inhibitors.

Bioorganic Chemistry published new progress about Chemiluminescent probes. 115144-35-9 belongs to class thiazole, and the molecular formula is C11H7KN2O3S2, Safety of Potassium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylate.

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

Hoeing, Susanne; Yeh, Ting-Yu; Baumann, Matthias; Martinez, Nancy E.; Habenberger, Peter; Kremer, Lea; Drexler, Hannes C. A.; Kuechler, Philipp; Reinhardt, Peter; Choidas, Axel; Zischinsky, Mia-Lisa; Zischinsky, Gunther; Nandini, Swaran; Ledray, Aaron P.; Ketcham, Stephanie A.; Reinhardt, Lydia; Abo-Rady, Masin; Glatza, Michael; King, Stephen J.; Nussbaumer, Peter; Ziegler, Slava; Klebl, Bert; Schroer, Trina A.; Schoeler, Hans R.; Waldmann, Herbert; Sterneckert, Jared published the artcile< Dynarrestin, a Novel Inhibitor of Cytoplasmic Dynein>, Computed Properties of 2222768-84-3, the main research area is esophageal squamous cell carcinoma proliferation cytoplasmic dynein dynarrestin; ciliary transport; ciliobrevin; dynein; glioblastoma; hedgehog; intraflagellar transport; phenotypic screening; stem cell-based phenotypic screening; vismodegib.

Aberrant hedgehog (Hh) signaling contributes to the pathogenesis of multiple cancers. Available inhibitors target Smoothened (Smo), which can acquire mutations causing drug resistance. Thus, compounds that inhibit Hh signaling downstream of Smo are urgently needed. We identified dynarrestin, a novel inhibitor of cytoplasmic dyneins 1 and 2. Dynarrestin acts reversibly to inhibit cytoplasmic dynein 1-dependent microtubule binding and motility in vitro without affecting ATP hydrolysis. It rapidly and reversibly inhibits endosome movement in living cells and perturbs mitosis by inducing spindle misorientation and pseudoprometaphase delay. Dynarrestin reversibly inhibits cytoplasmic dynein 2-dependent intraflagellar transport (IFT) of the cargo IFT88 and flux of Smo within cilia without interfering with ciliogenesis and suppresses Hh-dependent proliferation of neuronal precursors and tumor cells. As such, dynarrestin is a valuable tool for probing cytoplasmic dynein-dependent cellular processes and a promising compound for medicinal chem. programs aimed at development of anti-cancer drugs.

Cell Chemical Biology published new progress about Animal gene Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (GLI1). 2222768-84-3 belongs to class thiazole, and the molecular formula is C22H23F2N3O2S, Computed Properties of 2222768-84-3.

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