Month: October 2022

Wahyudi, Hendra; Tantisantisom, Worawan; Liu, Xuechao; Ramsey, Deborah M.; Singh, Erinprit K.; McAlpine, Shelli R. published the artcile< Synthesis, structure-activity analysis, and biological evaluation of sanguinamide B analogues>, Quality Control of 96929-05-4, the main research area is sanguinamide B analog synthesis antibacterial structure activity twitching motility; natural product antibiotic sanguinamide conformation conformer; peptide coupling Hantzsch cyclocondensation macrocyclization.

We report the first synthesis of sanguinamide B analogs. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogs all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogs showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a ‘pseudoequatorial’ position, and all other energy considerations are secondary.

Journal of Organic Chemistry published new progress about Antibacterial agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Quality Control of 96929-05-4.

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

Lam, P. Y. S.; Deudon, S.; Hauptman, E.; Clark, C. G. published the artcile< α-Nitrogen-activating effect in the room temperature copper-promoted N-arylation of heteroaryl carboxamides with phenylsiloxane or 4-tolylboronic acid>, Product Details of C5H6N2OS, the main research area is nitrogen heteroaromatic carboxamide phenylsiloxane arylation; tolylboronate nitrogen heteroaromatic carboxamide arylation; cross coupling nitrogen heteroaromatic carboxamide phenylsiloxane.

α-N-containing heteroaryl carboxamides undergo Cu-promoted N-phenylation with hypervalent PhSi(OMe)3 at room temperature, in the absence of base and in air. Arylboronic acid can substitute for PhSi(OMe)3 as the organometalloid. The α-heteroatom chelating effect is in the decreasing order of N > O, S. This discovery opens up the possibility of using other α-N functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation.

Tetrahedron Letters published new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (heteroaromatic). 31825-95-3 belongs to class thiazole, and the molecular formula is C5H6N2OS, Product Details of C5H6N2OS.

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

Cheng, Hongmei; Zang, Cuicui; Bian, Fengxia; Jiang, Yanke; Yang, Lin; Dong, Fan; Jiang, Heyan published the artcile< Boosting free radical type photocatalysis over Pd/Fe-MOFs by coordination structure engineering>, Related Products of 198904-53-9, the main research area is photocatalysis photocatalytic arylation decarboxylation cross coupling; palladium iron metal organic framework.

The development of novel heterogeneous photocatalytic systems, along with a deep understanding of the relationship between the catalytic center chem. environment and the catalytic performance, is of great significance. Herein, the surface microenvironment of Pd nanoparticles was modulated with engineered Fe-MOF coordination structures (octahedron MIL-100(Fe), concave octahedron MIL-101(Fe) and irregular lumpy MIL-53(Fe)). Two heterogeneous free radical photocatalytic organic transformations have been developed over Pd nanoparticle loaded Fe-MOFs (Pd/Fe-MOFs). The photocatalytic C-H arylation of thiazole and decarboxylation cross-coupling with cinnamic acid were investigated. Thiazole C-H arylation with halobenzenes was brought about through C-halogen bond activation with the photogenerated electron-rich Pd NPs, the aryl radical generation and the follow-up radical addition The cinnamic acid decarboxylation cross-coupling was also achieved by means of C-halogen bond activation with photogenerated electron-rich Pd NPs. The base regulated the product stereoselectivity by affecting the balance between cinnamic acid and carboxylate anions, as well as the balance between aryl radicals and the coordination complex intermediates. The improvement of the heterogeneous photocatalytic performance for thiazole C-H arylation and cinnamic acid decarboxylation cross-coupling should be ascribed to the difference in the electron transfer efficiency to Pd NPs over various engineered Fe-O cluster coordination structures. This work highlights the importance of exploiting structure engineering for heterogeneous photocatalytic systems.

Catalysis Science & Technology published new progress about Arylation (photocatalytic, C-H). 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Related Products of 198904-53-9.

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

Kim, Ho Shin; Hammill, Jared T.; Scott, Daniel C.; Chen, Yizhe; Rice, Amy L.; Pistel, William; Singh, Bhuvanesh; Schulman, Brenda A.; Guy, R. Kiplin published the artcile< Improvement of Oral Bioavailability of Pyrazolo-Pyridone Inhibitors of the Interaction of DCN1/2 and UBE2M>, Formula: C4H3NOS, the main research area is carcinoma DCN1 UBE2M interaction inhibitors NEDD8 pharmacokinetic oral bioavailability.

The cullin-RING ubiquitin ligases (CRLs) are ubiquitin E3 enzymes that play a key role in controlling proteasomal degradation and are activated by neddylation. We previously reported inhibitors that target CRL activation by disrupting the interaction of defective in cullin neddylation 1 (DCN1), a CRL neddylation co-E3, and UBE2M, a neddylation E2. Our first-generation inhibitors possessed poor oral bioavailability and fairly rapid clearance that hindered the study of acute inhibition of DCN-controlled CRL activity in vivo. Herein, we report studies to improve the pharmacokinetic performance of the pyrazolo-pyridone inhibitors. The current best inhibitor, 40 (I), inhibits the interaction of DCN1 and UBE2M, blocks NEDD8 transfer in biochem. assays, thermally stabilizes cellular DCN1, and inhibits anchorage-independent growth in a DCN1 amplified squamous cell carcinoma cell line. Addnl., we demonstrate that a single oral 50 mg/kg dose sustains plasma exposures above the biochem. IC90 for 24 h in mice.

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

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

Aihara, Kazuhiro; Kano, Yuko; Shiokawa, Sohjiro; Sasaki, Toshiro; Setsu, Fumihito; Sambongi, Yumiko; Ishii, Miyuki; Tohyama, Kazuyo; Ida, Takashi; Tamura, Atsushi; Atsumi, Kunio; Iwamatsu, Katsuyoshi published the artcile< CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure-Activity Relationships>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is methylcarbapenem antimicrobial activity.

A series of 1β-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogs showed potent antibacterial activities against Gram-pos. bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-neg. bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, i.e., imipenem (IPM), panipenem (PAPM), and meropenem (MEPM).

Bioorganic & Medicinal Chemistry published new progress about Antimicrobial agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

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

Jiang, Cheng; Yuan, Zhi; Wang, Ju-Fei; Fu, Jie; Jiang, Guang-Jun; Zheng, Liang-Rong published the artcile< Design of novel thiazole bearing pyrazole derivatives and their dual activities as ACE inhibitors and calcium channel blockers in cardiovascular disease>, Electric Literature of 57493-24-0, the main research area is cardiovascular disease thiazole pyrazole derivative ACE inhibitor calcium channel.

In an attempt to develop drugs for cardio-vascular disease, present manuscript deal with the development of dual acting agents targeting angiotensin converting enzyme (ACE) and calcium channel to treat hypertension. These mols. were developed via efficient multi-step synthetic route in excellent yield. In ACE inhibitors assay, these compounds showed considerable percentage of inhibition (32-94 %) with IC50 = 1.2 and 1.5 μM for most promising compound 6e and 6o, resp. In mol. docking study with ACE, compound 6e revealed similar fashion of mol. interaction with catalytic residues His353, Ala 354, Tyr 523, Tyr 520, and Glu 152, comparable with standard lisinopril. Addnl., in rat aortic strip model, these mols. significantly induce vasorelaxation via inhibiting Ca2+ channel in dose dependent manner.

Latin American Journal of Pharmacy published new progress about Angiotensin-converting enzyme inhibitors. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Electric Literature of 57493-24-0.

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

Doughty, Michael B.; Risinger, G. E.; Jungk, Steven J. published the artcile< Chemistry of the tricyclic form of thiamin with aldehydes in basic ethanol>, COA of Formula: C7H9NO2S, the main research area is thiamin aldehyde reaction; hydroxybenzylthiamin; pyrimidinylmethylfurothiazole; furothiazole pyrimidinylmethyl.

Upon the addition of PhCHO to basic thiamin solution gives an intermediate accumulates which gives rise to 2-(1-hydroxyphenylmethyl)thiamin-HCl upon acidification of the reaction mixture and high yields of both 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-benzoyl-3a-methylperhydrofuro[2,3-d]thiazole and benzoin when the reaction mixture is stirred for 5 h. Given that thiamin is unstable under these conditions such that it is converted completely to its tricyclic species, the 2-(1-hydroxyalkyl)thiamin salts, which have an increased base lability due to the addition of a C-2/N-3 torsional interaction to the base-labile thiazolium ring, would also not be expected to accumulate in appreciable concentrations under identical conditions. Based on product isolation and the synthesis of 2-benzoyl-3,4-dimethyl-5-ethoxycarbonyl-[2H]-thiazoline in the reaction of 3,4-dimethyl-5-ethyoxycarbonylthiazolium iodide with PhCHO in basic MeOH, the intermediate which accumulates during the reaction of the tricyclic form of thiam with PhCHO is a 2-benzoylthiazoline in equilibrium with a low concentration of its enol isomer. Reasons for the increased catalytic power of thiamin under these conditions, as well as the relevance of this chem. to the active site chem. of thiamin pyrophosphate, are discussed.

Bioorganic Chemistry published new progress about 20582-55-2. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, COA of Formula: C7H9NO2S.

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

Guggilapu, Sravanthi Devi; Guntuku, Lalita; Reddy, T. Srinivasa; Nagarsenkar, Atulya; Sigalapalli, Dilep Kumar; Naidu, V. G. M.; Bhargava, Suresh K.; Bathini, Nagendra Babu published the artcile< Synthesis of thiazole linked indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors>, Safety of Ethyl 2-amino-5-methylthiazole-4-carboxylate, the main research area is thiazole indole glyoxylamide preparation tubulin polymerization inhibitor anticancer; Anticancer; Apoptosis; Indolyl-3-glyoxylamide; Thiazole; Tubulin polymerization inhibitor.

A series of thiazole linked indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 13d (I) displayed cytotoxicity of IC50 = 93 nM towards DU145 cancer cell line. The most active compound 13d was also tested on RWPE-1 cells and was found to be safe compared to the DU145 cells. The target compounds were also evaluated for their inhibition activity of tubulin polymerization Further, the treatment of compound 13d on DU145 cells led to the inhibition of cell migration ability. The detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 13d induced apoptosis in DU145 cells. The influence of the cytotoxic compound 13d on the cell cycle distribution was assessed on the DU145 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, the treatment with compound 13d caused collapse of mitochondrial membrane potential and elevated intracellular ROS levels in DU145 cells. The results from mol. modeling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Thus, this new mol. scaffold could be a new lead for the development of anticancer agents that target tubulin.

European Journal of Medicinal Chemistry published new progress about Amides, oxo Role: PAC (Pharmacological Activity), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), PREP (Preparation), USES (Uses). 72054-60-5 belongs to class thiazole, and the molecular formula is C7H10N2O2S, Safety of Ethyl 2-amino-5-methylthiazole-4-carboxylate.

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

Tissaoui, Khalil; Raouafi, Noureddine; Boujlel, Khaled published the artcile< Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives>, Formula: C10H9NOS2, the main research area is rhodanine carbamodithioate benzylic electrosynthesis.

Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochem. reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with Et 3-bromopropionate or with Et 2-bromoacetate yields the corresponding carbamodithioates R1NHC(S)SCH2CH2CO2Et (R1 = PhCH2, 2-ClC6H4CH2, 2-pyridylmethyl, etc.) or cyclic rhodanines I (R2 = PhCH2, 2-ClC6H4CH2, 3-furylmethyl, etc.), resp. The effect of the amount of electrogenerated base on the yield of reaction was also evaluated.

Journal of Sulfur Chemistry published new progress about Aralkyl amines Role: RCT (Reactant), RACT (Reactant or Reagent). 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Formula: C10H9NOS2.

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

Liu, Pei-Han; Urban, Pawel L. published the artcile< Spontaneous luminescence color change in the firefly luciferase assay system>, Application of C11H7KN2O3S2, the main research area is luminescence color firefly luciferase; ATP assay; Color switching; Luciferase; Luminescence.

The temporal effects of luciferase reaction luminescence have only been discussed in the context of light intensity (flash vs. glow). However, alterations in the color of the light emitted over the luciferase reaction have not been reported. Here, the authors show a temporal change in the light color emitted during the reaction catalyzed by unmodified firefly luciferase when concentrations of one of the substrates, ATP, are gradually increased. The temporal color change from green to red occurs within the first few minutes of the luciferase reaction when an ATP-containing solution is either added or synthesized in situ with the aid of an autocatalytic reaction occurring simultaneously. This color change is not accompanied by pH changes. An anal. of the red and green channels demonstrates dissimilar kinetics, suggesting the coexistence of two or more temporally shifted luminescence pathways. The implications of these findings might improve dual-color biosensing/imaging protocols and influence the engineering of biophotonic systems.

Analytical Biochemistry published new progress about Color. 115144-35-9 belongs to class thiazole, and the molecular formula is C11H7KN2O3S2, Application of C11H7KN2O3S2.

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