Day: October 11, 2022

Barton, Anne; Breukelman, Stephen P.; Kaye, Perry T.; Meakins, G. Denis; Morgan, David J. published the artcile< The preparation of thiazole-4- and -5-carboxylates, and an infrared study of their rotational isomers>, Category: thiazole, the main research area is cyclocondensation thiourea bromomethyloxopentanoate; isobutyraldehyde chloroacetate cyclocondensation thiourea; aminoispropylthiazolecarboxylate methyl; butylthiazolecarboxylate ethyl; thiazolecarboxylate preparation rotational isomerism IR.

A general procedure is reported for the preparation of thiazole-4- and -5-carboxylates containing alkyl and halo substituents. Treatment of Me2CHCHO and Cl2CHCO2Me with NaOMe in Et2O at 0°, followed by addition of (H2N)2CS and 4 h reflux in MeOH gave the aminothiazole I. The thiazole II was prepared by treatment of EtO2CCHBrCOCMe3 with (H2N)2CS in refluxing EtOH for 1 h, followed by deamination with NaNO2-H3PO2. Both series of esters show IR carbonyl doublets caused by rotational isomerism; the more intense absorptions of the 4-carboxylates are at lower wave number, whereas those of the 5-carboxylates are the higher wave number component. In both series, the stronger bands arise from the thermochem. more stable forms. For the 4-carboxylates, these forms are the carbonyl O,S-syn-s-trans-rotamers.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 72054-60-5 belongs to class thiazole, and the molecular formula is C7H10N2O2S, Category: thiazole.

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

Powers, Jay P.; Piper, Derek E.; Li, Yang; Mayorga, Veronica; Anzola, John; Chen, James M.; Jaen, Juan C.; Lee, Gary; Liu, Jinqian; Peterson, M. Greg; Tonn, George R.; Ye, Qiuping; Walker, Nigel P. C.; Wang, Zhulun published the artcile< SAR and Mode of Action of Novel Non-Nucleoside Inhibitors of Hepatitis C NS5b RNA Polymerase>, COA of Formula: C10H9NOS2, the main research area is nonnucleoside inhibitor thioxothiazolidine aryl derivative hepatitis C NS5b polymerase.

Novel non-nucleoside inhibitors of the HCV RNA polymerase (NS5b) with sub-micromolar biochem. potency have been identified which are selective for the inhibition of HCV NS5b over other polymerases. The structures of the complexes formed between several of these inhibitors and HCV NS5b were determined by x-ray crystallog., and the inhibitors were found to bind in an allosteric binding site sep. from the active site. Structure-activity relationships and structural studies have identified the mechanism of action for compounds in this series, several of which possess drug-like properties, as unique, reversible, covalent inhibitors of HCV NS5b.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, COA of Formula: C10H9NOS2.

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

He, Xiao-Yang; Zou, Peng; Qiu, Jiayin; Hou, Ling; Jiang, Shibo; Liu, Shuwen; Xie, Lan published the artcile< Design, synthesis and biological evaluation of 3-substituted 2,5-dimethyl-N-(3-(1H-tetrazol-5-yl)phenyl)pyrroles as novel potential HIV-1 gp41 inhibitors>, Product Details of C10H9NOS2, the main research area is gp41 inhibitor HIV 1 antiviral tetrazolylphenylpyrrole preparation; pyrrole tetrazolylphenyl preparation gp41 inhibitor HIV 1 antiviral.

Based on the structure of HIV-1 gp41 binding site for small-mol. inhibitors, optimization of a lead compound resulted in the discovery of a new series of 2,5-dimethyl-3-(5-(N-phenylrhodaninyl)methylene)-N-(3-(1H-tetrazol-5-yl)phenyl)pyrrole compounds with improved anti-HIV-1 activity. The two most active compounds exhibited significant potency against gp41 6-HB formation with IC50 values of 4.4 and 4.6 μM and against HIV-1 replication in the MT-2 cells with EC50 values of 3.2 and 2.2 μM, resp., thus providing a new starting point to develop highly potent small-mol. HIV fusion inhibitors targeting gp41.

Bioorganic & Medicinal Chemistry published new progress about AIDS (disease). 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

Ogretir, Cemil; Demirayak, Seref; Duran, Murat published the artcile< Spectroscopic Determination and Evaluation of Acidity Constants for Some Drug Precursor 2-Amino-4-(3- or 4-substituted phenyl) Thiazole Derivatives>, Product Details of C9H7N3O2S, the main research area is spectroscopic determination acidity constant drug precursor amino phenyl thiazole.

Acid dissociation constants, Ka, of eight drug precursor 2-amino-4-(3- or 4-substituted phenyl) thiazole derivatives were determined using a UV-vis spectroscopic technique. The obtained Ka values were evaluated by structure elucidation and a protonation mechanism. The obtained tautomerization equilibrium constants, KT, indicated the predominance of amino forms for all studied compounds

Journal of Chemical & Engineering Data published new progress about Bond angle, dihedral. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Product Details of C9H7N3O2S.

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

Healy, Alan R.; Vizcaino, Maria I.; Crawford, Jason M.; Herzon, Seth B. published the artcile< Convergent and Modular Synthesis of Candidate Precolibactins. Structural Revision of Precolibactin A>, Application In Synthesis of 96929-05-4, the main research area is precolibactin convergent modular synthesis structure revision.

The colibactins are hybrid polyketide-nonribosomal peptide natural products produced by certain strains of commensal and extraintestinal pathogenic Escherichia coli. The metabolites are encoded by the clb gene cluster as prodrugs termed precolibactins. Clb+E. coli induce DNA double-strand breaks in mammalian cells in vitro and in vivo and are found in 55-67% of colorectal cancer patients, suggesting that mature colibactins could initiate tumorigenesis. However, elucidation of their structures has been an arduous task as the metabolites are obtained in vanishingly small quantities (μg/L) from bacterial cultures and are believed to be unstable. Herein we describe a flexible and convergent synthetic route to prepare advanced precolibactins and derivatives The synthesis proceeds by late-stage union of two complex precursors (e.g., 28 + 17 → 29a, 90%, represented in the graphic as I + II → III) followed by a base-induced double dehydrative cascade reaction to form two rings of the targets (e.g., 29a → 30a, 79%, III → IV). The sequence has provided quantities of advanced candidate precolibactins that exceed those obtained by fermentation, and is envisioned to be readily scaled. These studies have guided a structural revision of the predicted metabolite precolibactin A (to 7) and have confirmed the structures of the isolated metabolites precolibactins B (3) and C (6). Synthetic precolibactin C (6) was converted to N-myristoyl-D-asparagine and its corresponding colibactin by colibactin peptidase ClbP. The synthetic strategy outlined herein will facilitate mechanism of action and structure-function studies of these fascinating metabolites, and is envisioned to accommodate the synthesis of addnl. (pre)colibactins as they are isolated.

Journal of the American Chemical Society published new progress about Cyclocondensation reaction (base-induced double dehydrative cascade). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Application In Synthesis of 96929-05-4.

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

Peixoto, Philippe A.; Severin, Rene; Tseng, Chih-Chung; Chen, David Y.-K. published the artcile< Formal Asymmetric Synthesis of Echinopine A and B>, Computed Properties of 171877-39-7, the main research area is echinopine sesquiterpene enantioselective formal synthesis cyclization palladium catalyst; Diels Alder reaction echinopine sesquiterpene enantioselective formal synthesis.

The asym. formal synthesis of (+)-echinopines A and B was accomplished. Particularly noteworthy were the cascade construction of the [5,6,7]tricyclic ring system I (R = SiMe2CMe3) from the acyclic enyne precursor (2Z,6R,7R)-H2C:CHCH(CH2CH2CH:CH2)CH(OSiMe2CMe3)(CH2)2CH:CHCO2Me through a palladium-catalyzed cycloisomerization with subsequent intramol. Diels-Alder reaction, and the strategic application of a late-stage ring contraction of epoxy ketone II (R = SiMe2CMe3).

Angewandte Chemie, International Edition published new progress about Cyclization. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Computed Properties of 171877-39-7.

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

Tohidnezhad, Mersedeh; Kubo, Yusuke; Lichte, Philipp; Heigl, Tobias; Roch, Diana; Pour, Nazanin Barahmand; Bergmann, Christian; Soenmez, Tolga Taha; Hock, Jennifer Vanessa Phi; Fragoulis, Athanassios; Gremse, Felix; Rosenhain, Stefanie; Slowik, Alexander; Bienert, Michaela; Kweider, Nisreen; Wruck, Christoph Jan; Jahr, Holger; Hildebrand, Frank; Pape, Hans Christoph; Neu, Sabine; Fischer, Horst; Pufe, Thomas published the artcile< Effects of strontium-doped β-tricalcium scaffold on longitudinal nuclear factor-kappa beta and vascular endothelial growth factor receptor-2 promoter activities during healing in a murine critical-size bone defect model>, Formula: C11H8N2O3S2, the main research area is strontium doped tricalcium scaffold nuclear factor kappa beta; vascular endothelial growth factor receptor healing murine bone defect; NF-κB; VEGFR-2; bioluminescence; large bone defects; strontium; β-tricalcium phosphate.

It was hypothesized that strontium (Sr)-doped β-tricalcium phosphate (TCP)-based scaffolds have a pos. effect on the regeneration of large bone defects (LBD). Readouts in our mice models were nuclear factor-kappa beta (NF-κB) activity and vascular endothelial growth factor receptor-2 (VEGFR-2) promoter activity during the healing process. A 2-mm critical-size femoral fracture was performed in transgenic NF-κB- and VEGFR-2-luciferase reporter mice. The fracture was filled with a 3D-printed β-TCP scaffold with or without Sr. A bioluminescence in-vivo imaging system was used to sequentially investigate NF-κB and VEGFR-2 expression for two months. After sacrifice, soft and osseous tissue formation in the fracture sites was histol. examined NF-κB activity increased in the β-TCP + Sr group in the latter stage (day 40-60). VEGFR-2 activity increased in the + Sr group from days 0-15 but decreased and showed significantly less activity than the β-TCP and non-scaffold groups from days 40-60. The new bone formation and soft tissue formation in the + Sr group were significantly higher than in the β-TCP group, whereas the percentage of osseous tissue formation in the β-TCP group was significantly higher than in the β-TCP + Sr group. We analyzed longitudinal VEGFR-2 promoter activity and NF-κB activity profiles, as resp. agents of angiogenesis and inflammation, during LBD healing. The extended inflammation phase and eventually more rapid resorption of scaffold caused by the addition of strontium accelerates temporary bridging of the fracture gaps. This finding has the potential to inform an improved treatment strategy for patients who suffer from osteoporosis.

International Journal of Molecular Sciences published new progress about Angiogenesis. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Formula: C11H8N2O3S2.

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

Mack, Daniel J.; Isoe, Jun; Miesfeld, Roger L.; Njardarson, Jon T. published the artcile< Distinct biological effects of golgicide a derivatives on larval and adult mosquitoes>, Quality Control of 1003-32-3, the main research area is golgicide A derivative larvicidal insecticide mosquito larva.

A collection of Golgicide A (GCA) analogs has been synthesized and evaluated in larval and adult mosquito assays. Com. available GCA is a mixture of four compounds One enantiomer (GCA-2) of the major diastereomer in this mixture was shown to be responsible for the unique activity of GCA. Structure-activity studies (SAR) of the GCA architecture suggested that the pyridine ring was most easily manipulated without loss or gain in new activity. Eighteen GCA analogs were synthesized of which five displayed distinct behavior between larval and adult mosquitos, resulting in complete mortality of both Aedes aegypti and Anopheles stephensi larvae. Two analogs from the collection were shown to be distinct from the rest in displaying high selectivity and efficiency in killing An. stephensi larvae.

Bioorganic & Medicinal Chemistry Letters published new progress about Aedes aegypti. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Quality Control of 1003-32-3.

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

Yu, Jeongjae; Armstrong, Daniel W.; Ryoo, Jae Jeong published the artcile< Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations>, Name: (S)-4-Benzylthiazolidine-2-thione, the main research area is chiral HPLC stationary phase synthesis peptide coupling amino acid; phenylglycinol phenylglycine leucine phenyl amide HPLC stationary phase silica; HPLC enantioseparation aromatic compound; (R)-phenylglycine; (S)-leucine; (S)-leucinol; C3 symmetry; HPLC; N-phenyl amide; chiral stationary phases.

We recently reported a new C3-sym. (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatog. (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation In this study, three new C3-sym. CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-sym. CSPs (CSP 2-CSP 4).

Chirality published new progress about Amino acids Role: RCT (Reactant), RACT (Reactant or Reagent). 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Name: (S)-4-Benzylthiazolidine-2-thione.

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

Moszczynski-Petkowski, Rafal; Majer, Jakub; Borkowska, Malgorzata; Bojarski, Lukasz; Janowska, Sylwia; Matloka, Mikolaj; Stefaniak, Filip; Smuga, Damian; Bazydlo, Katarzyna; Dubiel, Krzysztof; Wieczorek, Maciej published the artcile< Synthesis and characterization of novel classes of PDE10A inhibitors - 1H-1,3-benzodiazoles and imidazo[1,2-a]pyrimidines>, Quality Control of 1003-32-3, the main research area is triazolopyridine pyrazolopyridine benzodiazole imidazopyrimidine preparation PDE10A enzyme inhibitor; 1H-1,3-benzodiazoles; Imidazo[1,2-a]pyrimidines; PDE10A.

New compounds containing [1,2,4]triazolo[1,5-a]pyridine I (R = 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl, 4,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl, 4-methylquinazolin-2-yl; R1 = Ph, pyrimidin-2-yl), pyrazolo[1,5-a]pyridine II (R = 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl, 4,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl; R1 = phenyl), 1H-1,3-benzodiazole III (R1 = 2-methoxyphenyl, pyridin-2-yl, 1,3-oxazol-4-yl, etc.; R2 = H, Me) and imidazo[1,2-a]pyrimidine IV backbones were designed and synthesized for PDE10A interaction. Among these compounds, 1H-1,3-benzodiazoles and imidazo[1,2-a]pyrimidines III and IV showed the highest affinity for PDE10A enzyme as well as good metabolic stability. Both classes of compounds were identified as selective and potent PDE10A enzyme inhibitors.

European Journal of Medicinal Chemistry published new progress about Benzimidazoles Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Quality Control of 1003-32-3.

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