Day: November 10, 2022

Breinholt, Jens published the artcileSynthesis of 2-amino-4H-thiazolo[5,4-b]indole and characterization of its colored conversion products with protein tyrosine phosphatase inhibitory activity, Category: thiazole, the main research area is thiazoloindolamine preparation reaction; protein tyrosine phosphatase inhibitor thiazoloindolamine reaction product.

In DMSO solution 2-amino-4H-thiazolo[5,4-b]indole (I) is converted to a complex mixture of colored products. The three major conversion end products, two of which are inhibitors of protein tyrosine phosphatases, were isolated by chromatog. methods and their structures characterized by spectroscopic anal., including NMR and MS combined with computer assisted structure elucidation, and, finally, confirmed by independent chem. synthesis. Synthesis of I as well as its N-acetyl derivatives from either oxindole or 2-bromo-1-(2-nitrophenyl)ethanone is described.

Journal of Heterocyclic Chemistry published new progress about thiazoloindolamine preparation reaction; protein tyrosine phosphatase inhibitor thiazoloindolamine reaction product. 90323-06-1 belongs to class thiazole, name is 4-(2-Nitrophenyl)thiazole-2-amine, and the molecular formula is C9H7N3O2S, Category: thiazole.

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

Kitir, Betul published the artcileTotal synthesis and structural validation of cyclodepsipeptides solonamide A and B, Safety of (S)-4-Benzylthiazolidine-2-thione, the main research area is cyclodepsipeptide solonamide A B total enantioselective synthesis antimicrobial; macrocycle virulence gene expression Staphylococcus aureus inhibitor cyclodepsipeptide; hydroxy acid stereoselective aldol reaction esterification acylation macrolactamization.

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chem. synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereoselective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochem. of the auxiliary in the aldol steps we gained access to the natural products as well as their β3-epimers.

Tetrahedron published new progress about Acylation. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Safety of (S)-4-Benzylthiazolidine-2-thione.

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

Peixoto, Philippe A. published the artcileFormal Asymmetric Synthesis of Echinopine A and B, Application of (S)-4-Benzylthiazolidine-2-thione, 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, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Application of (S)-4-Benzylthiazolidine-2-thione.

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

Royo, Santiago published the artcileAntiprotozoal and cysteine proteases inhibitory activity of dipeptidyl enoates, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is antiprotozoal cysteine protease inhibitor dipeptidyl enoate derivative preparation; Chagas disease; Cysteine proteases; Inhibitors; Malaria; Sleeping sickness.

A family of dipeptidyl enoates has been prepared and tested against the parasitic cysteine proteases rhodesain, cruzain and falcipain-2 related to sleeping sickness, Chagas disease and malaria, resp. They have also been tested against human cathepsins B and L1 for selectivity. Dipeptidyl enoates resulted to be irreversible inhibitors of these enzymes. Some of the members of the family are very potent inhibitors of parasitic cysteine proteases displaying k2nd (M-1s-1) values of seven orders of magnitude. In vivo antiprotozoal testing was also performed. Inhibitors exhibited IC50 values in the micromolar range against Plasmodium falciparum, Trypanosoma brucei, Trypanosoma cruzi and even more promising lower values against Leishmania donovanii.

Bioorganic & Medicinal Chemistry published new progress about Antimalarials. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

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

Lvov, Andrey G. published the artcilePhotorearrangement of dihetarylethenes as a tool for the benzannulation of heterocycles, Application In Synthesis of 16441-28-4, the main research area is bromo heteroarylethanone heteroaryl acetic acid cyclocondensation reaction; diheteroaryl furanone preparation tandem benzannulation photorearrangement; heteroaryl fused benzofuranone preparation crystal structure.

A general strategy for the preparative benzannulation of aromatic heterocycles via photocyclization of 1,2-dihetarylethenes was proposed for the first time. The strategy included two steps namely, modular assembly of dihetarylethenes from widely available 3-hetarylacetic acids and 2-bromo-1-hetarylethanones and subsequent preparative photorearrangement (using a UV lamp at 365 nm as the light source). This approach was efficient for the annulation of a wide range of heterocycles and provided C-, N-, O- or S-substituents in the benzoheterocycles obtained. The photochem. step was a metal-, acid- and oxidant-free reaction, which required non-inert conditions and easily monitored by NMR spectroscopy. Applicability of the proposed strategy was tested in the synthesis of a wide range of substituted carbazoles and benzo[b]thiophenes as well as on a gram-scale benzannulation of 3-indoleacetic acid. This study disclosed how to overcome two notable obstacles to the successful photorearrangement of dihetarylethenes: undesired reactions associated with photogenerated singlet oxygen and the instability of desired products. The first problem was successfully solved by the addition of DABCO, while development of an in-situ alkylation protocol to trap unstable photoproducts allowed us to overcome the second issue.

Organic & Biomolecular Chemistry published new progress about Benzannulation. 16441-28-4 belongs to class thiazole, name is 2-(2-Phenylthiazol-4-yl)acetic acid, and the molecular formula is C11H9NO2S, Application In Synthesis of 16441-28-4.

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

Minor-Villar, Leticia published the artcileDesulfurization-oxygenation of chiral 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and microwave irradiation, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is desulfurization oxygenation chiral thiazolidinethione oxazolidinethione propylene oxide microwave; thiazolidinone preparation; oxazolidinone preparation.

An efficient method for the desulfurization-oxygenation of 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and employing microwave irradiation is described. This strategy of oxygenation of the thiocarbonyl group provides an attractive methodol. to prepare chiral 1,3-thiazolidin-2-ones and 1,3-oxazolidin-2-ones from the corresponding precursors in good yields.

Synlett published new progress about Desulfurization. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

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

Button, Richard G. published the artcileDecarboxylation of heterocyclic acetic acids. II. Direct and indirect evidence for the zwitterionic mechanism, Product Details of C11H9NO2S, the main research area is pyridylacetate decarboxylation; heterocyclic acetate decarboxylation; tautomerism decarboxylation heterocycle; zwitterion decarboxylation heterocycle.

Microscopic and model pKa values were determined for 2- and 4-pyridylacetic acids in aqueous 2-propanol, and used to determine microscopic pKa values as a function of solvent composition Calculation of the mode fractions of zwitterionic and neutral forms allowed the decarboxylation rates to be reexpressed in terms of these species as kZ, and kN, resp. Correlation of kZ, but not kN, with solvent composition showed that decarboxylation is via the zwitterion. Similar calculations, with allowance for tautomerism, showed that 8 other heterocyclic acetic acids decarboxylate by the same mechanism. β-Keto acids may also decarboxylate via a zwitterion.

Journal of the Chemical Society, Perkin Transactions 11: Physical Organic Chemistry published new progress about Decarboxylation. 16441-28-4 belongs to class thiazole, name is 2-(2-Phenylthiazol-4-yl)acetic acid, and the molecular formula is C11H9NO2S, Product Details of C11H9NO2S.

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

Nagashima, Shinya published the artcileNovel quinuclidinyl heteroarylcarbamate derivatives as muscarinic receptor antagonists, Safety of Ethyl 4-phenylthiazole-5-carboxylate, the main research area is quinuclidinyl heteroarylcarbamate derivative preparation muscarinic receptor antagonist; ASP9133; COPD; In vivo selectivity; Long acting muscarinic receptor antagonist.

Herein, we describe the synthesis and pharmacol. profiles of novel quinuclidinyl heteroarylcarbamate derivatives Among them, the quinuclidin-4-yl thiazolylcarbamate derivative ASP9133 was identified as a promising long-acting muscarinic antagonist (LAMA) showing more selective inhibition of bronchoconstriction against salivation and more rapid onset of action in a rat model than tiotropium bromide.

Bioorganic & Medicinal Chemistry published new progress about Bronchodilators. 99822-80-7 belongs to class thiazole, name is Ethyl 4-phenylthiazole-5-carboxylate, and the molecular formula is C12H11NO2S, Safety of Ethyl 4-phenylthiazole-5-carboxylate.

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

Sparrow, Kevin John published the artcileStudies towards development of asymmetric double-Mannich reactions of chiral 2-oxocyclohexanecarboxylate derivatives with bis(aminol)ethers, SDS of cas: 171877-39-7, the main research area is azabicyclooctanecarboxylic acid imide ester preparation; nonracemic oxazolidinone imide ester oxocyclohexanecarboxylic acid preparation Mannich reaction; erbium lanthanum catalyst double Mannich reaction oxocyclohexanecarboxylate aminol ether; double Mannich reaction nonracemic oxazolidinone imide ester oxocyclohexanecarboxylic acid; azabicyclooctanecarbonyl methylphenyloxazolidinone mol crystal structure.

An improved method for the double-Mannich reaction of β-ketoesters and bis(aminol)ethers (EtOCH2)2NR (R = Et, PhCH2) in the presence of Er(OTf)3 or La(OTf)3 was developed. Esters of 2-oxocyclohexanecarboxylic acid with 8-phenylmenthol, pantolactone, and trans-2-phenylcyclohexanol and imides with norephedrine-, (S)-phenylalaninol-, and (S)-α,α-diphenylvalinol-derived oxazolidinones and oxazolidinethiones were prepared Double Mannich reaction of EtN(CH2OEt)2 with the oxocyclohexanecarboxylic acid esters and imides yielded mixtures of azabicyclooctanecarboxylic acid ester and imide diastereomers. The oxocyclohexanecarboxylic acid imide with a norephedrine-derived oxazolidinone and its derived azabicyclooctanecarboxylic acid imide product were separated into their diastereomers; the structures of both reactant imide diastereomers and the major azabicyclooctanecarboxylic acid imide diastereomer were assigned by X-ray crystallog.

Tetrahedron published new progress about Chiral auxiliary. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, SDS of cas: 171877-39-7.

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

Huang, David S. published the artcileSynthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is pironetin analog preparation anticancer structure activity ovarian cancer; Cytotoxicity; Pironetin; Structure-activity; Synthesis; Tubulin.

Pironetin is an α-tubulin-binding natural product with potent antiproliferative activity against several cancer cell lines that inhibits cell division by forming a covalent adduct with α-tubulin via a Michael addition into the natural product’s α,β-unsaturated lactone. We designed and prepared analogs carrying electron-withdrawing groups at the α-position (C2) of the α,β-unsaturated lactone with the goal to generate potent and selective binding analogs. We prepared derivatives I (R = F, Me, Cl, Br, Ph) containing halogens, a Ph, and a Me group at the C2 position to evaluate the structure-activity relationship at this position. Testing of the analogs in ovarian cancer cell lines demonstrated 100-1000-fold decreased antiproliferative activity.

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

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