Category: 171877-39-7

Feng, Xixi published the artcileStructure-Affinity Relationship Analysis of Selective FKBP51 Ligands, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is crystal structure FKBP protein psychiatric metabolic disorder.

The FK506-binding protein 51 (FKBP51) is a promising drug target for the treatment of stress-related psychiatric or metabolic disorders. Just recently, the first selective ligands for FKBP51 were reported based on an induced fit mechanism, but they are too large for a further drug development process. The authors therefore designed and synthesized a novel series of selective ligands to explore the requirements necessary for binding to the induced-fit conformation. All ligands of this series show no binding toward the structurally very similar antitarget FKBP52. With the cocrystal structure of the best ligand in this novel series the authors confirmed the induced fit mechanism. Furthermore, the structure-affinity relationship provides information about beneficial structural features, which is valuable for the development of improved FKBP51-directed drugs.

Journal of Medicinal Chemistry published new progress about Crystal structure. 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

Shi, Min published the artcileSynthesis of novel chiral Cu or Ag/S,N cluster complexes and absolute stereostructures as determined by X-ray crystallography, Name: (S)-4-Benzylthiazolidine-2-thione, the main research area is copper silver chiral thiazolidinethione ligand complex preparation structure; crystal structure copper silver chiral thiazolidinethione ligand complex.

Novel chiral Cu(I) and Ag(I) metal complexes were synthesized from the reaction of chiral (S)-(-)-4-benzyl-1,3-thiazolidine-2-thione ligand with CuCl and AgOAc in CH2Cl2 in the presence of Et3N and DMAP at room temperature Their unique crystal structures were determined by x-ray anal. Four Cu(I) atoms and four 1,3-thiazolidine-2-thione ligands form a butterfly-type metal cluster. Six Ag(I) atoms and six 1,3-thiazolidine-2-thione ligands form another butterfly-type cluster.

Chirality published new progress about Crystal structure. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Name: (S)-4-Benzylthiazolidine-2-thione.

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

Shi, Min published the artcileSynthesis of a novel copper(II) complex and its crystal structure, COA of Formula: C10H11NS2, the main research area is copper thiazolidinethione complex preparation structure; crystal structure copper thiazolidinethione complex.

One novel chiral Cu(II) complex was successfully synthesized from the reaction of chiral 1,3-thiazolidine-2-thione ligand with CuCl2 in CH2Cl2 in the presence of Et3N and DMAP at room temperature Its unique crystal structure was unambiguously disclosed by x-ray anal. The crystal is tetragonal, space group I4(1), a 15.0875(11), b 15.0875(11), c 19.362(3) Å, V = 4407.4(8) A3, Z = 8, ρcalc = 1.639 mg cm-3.

Journal of Organometallic Chemistry published new progress about Crystal structure. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, COA of Formula: C10H11NS2.

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

Marson, Charles M. published the artcileDiscovery of Potent, Isoform-Selective Inhibitors of Histone Deacetylase Containing Chiral Heterocyclic Capping Groups and a N-(2-Aminophenyl)benzamide Binding Unit, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is aminophenylbenzamide pyrimidine imidazolinone thiazoline capped preparation histone deacetylase inhibition; thiazoline capped HDAC3 NCoR1 inhibitor preparation antitumor activity apoptosis.

The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzamide I gave resp. IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)benzamides previously reported, an example of each ring system at 1 μM causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by I was observed, with resp. IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.

Journal of Medicinal Chemistry 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

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

Bumbu, Valentina D. published the artcileKinetic Resolution of N-Acyl-Thiolactams via Catalytic Enantioselective Deacylation, Computed Properties of 171877-39-7, the main research area is kinetic resolution acyl thiolactam catalytic enantioselective deacylation benzotetramisole.

Methanolysis of N-acylthiazolidin-2-thiones and -oxazolidin-2-thiones in the presence of acyl transfer catalyst benzotetramisole (BTM) proceeds in a highly enantioselective fashion thus enabling kinetic resolution of these substrates [e.g., treatment of thiolactam (±)-I with MeOH, catalyst II and PhCO2H afforded (S)-III + (R)-I with s = 84].

Organic Letters published new progress about Acylation catalysts (stereoselective). 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

Wu, Yikang published the artcileEnantioselective Total Synthesis of (+)-Brefeldin A and 7-epi-Brefeldin A, Application In Synthesis of 171877-39-7, the main research area is asym synthesis brefeldin a epibrefeldin stereoselective aldol chiral auxiliary; chiral auxiliary oxazolidinone thiazolidinethione stereoselective aldol reaction protecting group; stereoselective reduction elimination solvent effect asym synthesis brefeldin a; intramol Mukaiyama aldol condensation stereoselective Michael asym synthesis brefeldin.

A convergent enantioselective route to brefeldin A (I) and 7-epi-BFA was developed. The key C-4/C-5 chiral centers were established by using chiral auxiliary induced intermol. asym. aldolization in the presence of TiCl4 and TMEDA. The results with the thiazolidinethione/TiCl4 mediated intermol. asym. aldolization added some new information about the scope and limitations to the existing knowledge of that type of reactions (which so far was essentially limited to the reactions with N-propionyl thiazolidinethiones). During the course a method for protecting the liable aldol hydroxyl groups by using inexpensive TBSCl in DMF with 2,6-lutidine as the base was developed to replace the otherwise unavoidable TBSOTf procedure. Due to the excessive steric hindrance, removal of the auxiliary was much more difficult than most literature cases. Cleavage of the oxazolidinone by reduction was almost impossible. The thiazolidinethione auxiliary was relatively easier to remove. However, several reactions reported for facile removal of thiazolidinethione auxiliaries in the literature still failed. Reductive removal of the thiazolidinethione auxiliary was most effectively realized with LiBH4 in di-Et ether in the presence of 1 equiv of MeOH (a modification of a literature procedure for removal of oxazolidinone auxiliaries in less hindered substrates). Apart from the auxiliary removal, oxidation of the alc. into aldehyde and the deprotection of the dithiolane protecting group were also rather difficult in the present context. A range of methods were screened before final solutions were found. The five-membered ring was constructed by employing an intramol. Mukaiyama reaction after many attempts with the intramol. aldolization under a variety of conditions failed. The rate of elimination of the alkoxyl to form the α,β-double bond of a key intermediate cyclopentenone with DBU was highly solvent dependent (very sluggish in CH2Cl2 but rather fast in MeOH). Introduction of the lower chain (which was synthesized by using a Jacobsen KHR to establish the C-15 chirality) was achieved through a Michael addition similar to the precedents in the literature. It has not been noticed before that the yield of this Michael reaction could be dramatically raised by using 3 equiv of the copper-lithium reagent. Reduction of the C-7 carbonyl was apparently more difficult than similar cases in the literature. After examination of many reagents under various conditions, it was found that the best reagent for yielding the α-isomer was (S)-2-methyl-CBS-borolidine/BH3 and that for the β-isomer was L-Selectride. The α- and β-isomers were then further elaborated into (+)-brefeldin A and 7-epi-BFA, resp. An unexpected yet very interesting solubility difference between BFA and 7-epi-BFA was also observed

Journal of Organic Chemistry published new progress about Aldol condensation, stereoselective. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

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

Lu, Cui-Fen published the artcileStereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, using (4S)-benzylthiazolidinethione as a chiral auxiliary, Category: thiazole, the main research area is methyltridecanone stereoselective synthesis Michael addition benzylthiazolidinethione chiral auxiliary.

The stereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, was carried out in 20.7% overall yield based on (4S)-benzylthiazolidine-2-thione (five steps). In the crucial step, the stereogenic center was generated by an asym. Michael addition using enantiomerically pure (4S)-benzylthiazolidine-2-thione as a chiral auxiliary.

Tetrahedron: Asymmetry published new progress about Michael reaction, stereoselective. 171877-39-7 belongs to class thiazole, name is (S)-4-Benzylthiazolidine-2-thione, and the molecular formula is C10H11NS2, Category: thiazole.

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

Aursnes, M. published the artcileStereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator, Safety of (S)-4-Benzylthiazolidine-2-thione, the main research area is protectin D1 stereoselective synthesis antiinflammatory proresolving lipid mediator; Wittig reaction Evans Aldol hydrogenation Lindlar catalyst chiral auxiliary.

A convergent stereoselective synthesis of the potent anti-inflammatory, proresolving and neuroprotective lipid mediator protectin D1 has been achieved in 15% yield over eight steps. The key features were a stereocontrolled Evans-aldol reaction with Nagao’s chiral auxiliary and a highly selective Lindlar reduction of internal alkyne (I) , allowing the sensitive conjugated E,E,Z-triene to be introduced late in the preparation of protectin D1. The UV and LC/MS-MS data of synthetic protectin D1 matched those obtained from endogenously produced material.

Organic & Biomolecular Chemistry published new progress about Aldol addition, stereoselective. 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