Month: November 2022

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

Huang, David S. published the artcileSynthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin, Computed Properties of 171877-39-7, the main research area is pironetin analog preparation antitumor structure activity; antitumor agents; natural products; tubulin binding agents; α,β-unsaturated lactones; α-tubulin.

Pironetin is a natural product with potent antiproliferative activity that forms a covalent adduct with α-tubulin via conjugate addition into the natural product’s α,β-unsaturated lactone. Although pironetin’s α,β-unsaturated lactone is involved in its binding to tubulin, the structure-activity relationship at different positions of the lactone have not been thoroughly evaluated. For a systematic evaluation of the structure-activity relationships at the C4 and C5 positions of the α,β-unsaturated lactone of pironetin, twelve analogs of the natural product, I (R1 = R2 = H, Me; R1 = Me, n-Pr, CH2CF3, cyclopropyl, iso-Bu, CH2Ph, iso-Pr, R2 = H; R1 = H, R1 = Et) and II (R1 = Et, R2 = H; R1 = H, R2 = Et), were prepared by total synthesis. Modifying the stereochem. at the C4 and/or C5 positions of the α,β-unsaturated lactone of pironetin resulted in loss of antiproliferative activity in OVCAR5 ovarian cancer cells. While changing the C4 Et substituent with groups such as Me, Pr, cyclopropyl, and iso-Bu were tolerated, groups with larger steric properties such as an iso-Pr and benzyl groups were not.

ChemMedChem 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, Computed Properties of 171877-39-7.

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

Kozikowski, Alan P. published the artcileChemistry, biology, and QSAR studies of substituted biaryl hydroxamates and mercaptoacetamides as HDAC inhibitors-nanomolar-potency inhibitors of pancreatic cancer cell growth, Name: 4-(2-Nitrophenyl)thiazole-2-amine, the main research area is histone deacetylase inhibitor biaryl hydroxamate mercaptoacetamide preparation QSAR; pancreatic cancer inhibitor biaryl hydroxamate mercaptoacetamide preparation QSA.

The histone deacetylases (HDACs) are able to regulate gene expression, and inhibitors of the HDACs (HDACIs) hold promise in the treatment of cancer as well as a variety of neurodegenerative diseases. To investigate the potential for isoform selectivity in the inhibition of HDACs, we prepared a small series of 2,4′-diaminobiphenyl ligands functionalized at the para-amino group with an appendage containing either a hydroxamate or a mercaptoacetamide group and coupled to an amino acid residue at the ortho-amino group. A smaller series of substituted phenylthiazoles was also explored. Some of these newly synthesized ligands show low-nanomolar potency in HDAC inhibition assays and display micromolar to low-nanomolar IC50 values in tests against five pancreatic cancer cell lines. The isoform selectivity of these ligands for class I HDACs (HDAC1-3 and 8) and class IIb HDACs (HDAC6 and 10) together with QSAR studies of their correlation with lipophilicity are presented. Of particular interest is the selectivity of the mercaptoacetamides for HDAC6.

ChemMedChem published new progress about Antitumor agents. 90323-06-1 belongs to class thiazole, name is 4-(2-Nitrophenyl)thiazole-2-amine, and the molecular formula is C9H7N3O2S, Name: 4-(2-Nitrophenyl)thiazole-2-amine.

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

Zhang, Qian published the artcileDiscovery of Triazolo-pyridazine/-pyrimidine Derivatives Bearing Aromatic (Heterocycle)-Coupled Azole Units as Class II c-Met Inhibitors, Application In Synthesis of 144060-99-1, the main research area is triazolopyridazine triazolopyrimidine preparation cMet kinase inhibition SAR anticancer human.

Two series of novel triazolo-pyridazine/-pyrimidine derivatives were designed, synthesized, and evaluated for their inhibitory activity against c-Met kinase, as well as three c-Met overexpressed cancer cell lines (A549, MCF-7, and HeLa) and one normal human hepatocytes cell line LO2 in vitro. The most promising compound I exhibited significant cytotoxicity against A549, MCF-7, and HeLa cell lines with IC50 values of 1.06 +/- 0.16, 1.23 +/- 0.18, and 2.73 +/- 0.33μM, resp. Moreover, the inhibitory activity of compound I against c-Met kinase (IC50 = 0.090μM) was equal to that of Foretinib (IC50 = 0.019μM). The result of the acridine orange single staining test demonstrated that compound I could remarkably induce apoptosis of A549 cells. The results of apoptosis and cycle distribution of cells showed that compound I could induce late apoptosis of A549 cells and stimulate A549 cells arresting in the G0/G1 phase. Structure-activity relationships (SARs), pharmacol. results, and docking studies indicated that the introduction of 5-methylthiazole fragment to the five-atom moiety was beneficial for the activity. So far, the existing data indicated that I may become a potential class II c-Met inhibitor.

ACS Omega published new progress about Antitumor agents. 144060-99-1 belongs to class thiazole, name is 2-(4-Fluorophenyl)-4-methylthiazole-5-carboxylic acid, and the molecular formula is C11H8FNO2S, Application In Synthesis of 144060-99-1.

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