Month: October 2022

Yamada, Shinji; Yamagami, Kaoru; Oaku, Saki published the artcile< [2+2] Photodimerization of (E)-styrylthiazoles through cation-π-controlled preorientation>, SDS of cas: 1003-32-3, the main research area is diphenyl thiazolyl cyclobutane preparation diastereoselective regioselective; styrylthiazole photodimerization.

Cation-π-controlled preorientation of (E)-styrylthiazoles RCH=CHC6H5 (R = 1,3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl) was performed in both solution and solid phases. Irradiation of (E)-styrylthiazoles in the presence of HCl produced synHT dimers I (R = 1,3-thiazol-2-yl, 1,3-thiazol-4-yl) in good selectivities, while little selectivity was observed without HCl. X-ray structures for the HCl salts of (E)-styrylthiazoles showed a head-to-tail arrangement through cation-π interactions between the two neighboring mols. Irradiation of these HCl salts produced synHT dimers I in excellent yields.

Tetrahedron Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, SDS of cas: 1003-32-3.

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

Teloxa, Saul F.; Kennington, Stuart C. D.; Camats, Marc; Romea, Pedro; Urpi, Felix; Aullon, Gabriel; Font-Bardia, Merce published the artcile< Direct, Enantioselective, and Nickel(II) Catalyzed Reactions of N-Azidoacetyl Thioimides with Trimethyl Orthoformate: A New Combined Methodology for the Rapid Synthesis of Lacosamide and Derivatives>, Electric Literature of 96-53-7, the main research area is Lacosamide derivative enantioselective preparation; azidoacetyl thioimide trimethyl orthoformate nickel catalyst addition reduction acylation; C−C bond forming reactions; asymmetric synthesis; catalysis; lacosamide; synthetic methods.

A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with tri-Me orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine was reported. The heterocyclic scaffold could be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides R1R2NC(O)CHN3CH(OMe)2 [R1 = n-hexyl, Ph, Bn, etc.; R2 = H; R1R2 = (CH2)4, (CH2)2O(CH2)2] in high yields. Appropriate manipulation of the N-benzyl amide derivative provided an efficient access to the antiepileptic agent lacosamide through a new enantioselective C-C bond-forming process. DFT computational studies uncover clues for the understanding of the remarkable stereocontrol of the addition of a nickel(II) enolate to a putative oxocarbenium intermediate from tri-Me orthoformate.

Chemistry – A European Journal published new progress about Acylation. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Electric Literature of 96-53-7.

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

Li, Ruixin; Xie, Hongguo; Zhang, Chunguang; Sun, Yeqing; Yin, Heng published the artcile< ROS-Responsive Polymeric Micelle for Improving Pesticides Efficiency and Intelligent Release>, Electric Literature of 96-53-7, the main research area is ROS responsive polymeric micelle controlled release fungicide validamycin Rhizoctonia; ROS-responsive; Rhizoctonia solani; biostimulation; polymeric micelle; validamycin.

The low utilization rate of pesticides causes serious problems such as food safety and environmental pollution. Stimulus-responsive release can effectively improve the utilization rate of pesticides. Reactive oxygen species (ROS) burst, as an early event of plant-pathogen interaction, can stimulate the release of pesticides. In this work, a polymeric micelle with ROS-responsive was prepared and then Validamycin (Vail) was loaded into polymeric micelle to prepare Vail-loaded polymeric micelle. The Vail-loaded polymeric micelle displayed excellent ROS-dependent release kinetics. In vitro and in vivo antifungal experiments confirmed that the Vail-loaded polymeric micelle could improve antifungal efficacy against Rhizoctonia solani than with the Vail reagent. Therefore, as a biostimulation and controlled release system, ROS-responsive polymeric micelles can improve the utilization rate of pesticides and alleviate the problem of food safety and environmental pollution.

Journal of Agricultural and Food Chemistry published new progress about Agrochemical fungicides. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Electric Literature of 96-53-7.

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

Karade, Hitendra; Sathe, Manisha; Kaushik, M. P. published the artcile< An efficient method for the synthesis of 2-aminothiazoles using silica chloride as a heterogeneous catalyst>, Category: thiazole, the main research area is aminothiazole preparation ketone thiourea silica chloride catalyst; thiazole amino preparation ketone thiourea silica chloride catalyst.

Preparation of 2-aminothiazoles under mild reaction conditions with quant. yields using silica chloride as an effective heterogeneous catalyst is reported.

Catalysis Communications published new progress about Cyclization. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Category: thiazole.

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

Chan, Yuk-Cheung; Sak, Marcus H.; Frank, Scott A.; Miller, Scott J. published the artcile< Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes>, SDS of cas: 1003-32-3, the main research area is heterocyclic tetrahydro carboline preparation enantioselective; benzylindolyl ethanamine carboxaldehyde Pictet Spengler squaramide carboxylic acid catalyst; Pictet-Spengler; cooperative catalysis; heterocycles; hydrogen bond donors; peptides.

Herein an organocatalytic enantioselective functionalization of heterocyclic carboxaldehydes RCHO (R = Ph, pyridin-3-yl, 1H-imidazol-2-yl, etc.) via the Pictet-Spengler reaction was reported. Through careful pairing of novel squaramide and Bronsted acid catalysts, this method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated β-(tetrahydro)carbolines I (R1 = Bn, 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, etc.) in good yield and enantioselectivity. Careful selection of carboxylic acid co-catalyst is essential for toleration of a variety of regioisomeric heterocycles I. Utility is demonstrated via the three-step stereoselective preparation of pyridine-containing analogs I (R = 5-chloropyridin-2-yl; R1 = 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, 2-carboxyethyl, carboxymethyl) of potent selective estrogen receptor downregulator and U.S. FDA approved drug Tadalafil.

Angewandte Chemie, International Edition published new progress about Amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, SDS of cas: 1003-32-3.

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

Huang, David S.; Wong, Henry L.; Georg, Gunda I. published the artcile< Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin>, Product Details of C10H11NS2, 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, and the molecular formula is C10H11NS2, Product Details of C10H11NS2.

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

Wang, Rubing; Chen, Chengsheng; Zhang, Xiaojie; Zhang, Changde; Zhong, Qiu; Chen, Guanglin; Zhang, Qiang; Zheng, Shilong; Wang, Guangdi; Chen, Qiao-Hong published the artcile< Structure-Activity Relationship and Pharmacokinetic Studies of 1,5-Diheteroarylpenta-1,4-dien-3-ones: A Class of Promising Curcumin-Based Anticancer Agents>, Safety of Thiazole-5-carboxyaldehyde, the main research area is pentadienone curcumin structure pharmacokinetics antitumor neoplasm.

Forty-three 1,5-diheteroaryl-1,4-pentadien-3-ones were designed as potential curcumin mimics, structurally featuring a central five-carbon dienone linker and two identical nitrogen-containing aromatic rings. They were synthesized using a Horner-Wadsworth-Emmons reaction as the critical step and evaluated for their cytotoxicity and antiproliferative activities toward both androgen-insensitive and androgen-sensitive prostate cancer cell lines and an aggressive cervical cancer cell line. Most of the synthesized compounds showed distinctly better in vitro potency than curcumin in the four cancer cell lines. The structure-activity data acquired from the study validated (1E,4E)-1,5-diheteroaryl-1,4-pentadien-3-ones as an excellent scaffold for in-depth development for clin. treatment of prostate and cervical cancers. 1-Alkyl-1H-imidazol-2-yl, ortho pyridyl, 1-alkyl-1H-benzo[d]imidazole-2-yl, 4-bromo-1-methyl-1H-pyrazol-3-yl, thiazol-2-yl, and 2-methyl-4-(trifluoromethyl)thiazol-5-yl were identified as optimal heteroaromatic rings for the promising in vitro potency. (1E,4E)-1,5-Bis(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one, featuring thiazole rings and trifluoromethyl groups, was established as the optimal lead compound because of its good in vitro potency and attractive in vivo pharmacokinetic profiles.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Safety of Thiazole-5-carboxyaldehyde.

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

Shahwar, Durre; Tahir, M. Nawaz; Raza, Muhammad Asam; Ahmad, Naeem; Aslam, Saherish published the artcile< 3-Benzyl-2-sulfanylidene-1,3-thiazolidin-4-one>, Safety of 3-Benzyl-2-thioxothiazolidin-4-one, the main research area is mol structure benzyl sulfanylidene thiazolidinone; crystal structure benzyl sulfanylidene thiazolidinone.

In the title compound, C10H9NOS2, the five-membered heterocyclic ring and the benzyl moiety are oriented at a dihedral angle of 77.25(4)°. In the crystal, infinite polymeric C(6) chains extending along [001] are formed due to C-H…O H bonds. C-H…π interactions link the chains, building up a three-dimensional network. Crystallog. data and at. coordinates are given.

Acta Crystallographica, Section E: Structure Reports Online published new progress about Crystal structure. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Safety of 3-Benzyl-2-thioxothiazolidin-4-one.

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

Takeda, Yasuyuki; Uoto, Kouichi; Iwahana, Michio; Jimbo, Takeshi; Nagata, Motoko; Atsumi, Ryo; Ono, Chiho; Tanaka, Noriko; Terasawa, Hirofumi; Soga, Tsunehiko published the artcile< New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 5>, Related Products of 1003-32-3, the main research area is taxoid preparation dihydrobaccatin acetal; taxane acetal preparation antitumor metabolic stability.

To improve the metabolic stability of I, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogs. Most of the synthetic compounds maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. And some compounds exhibited potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration similarly to I.

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Related Products of 1003-32-3.

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

He, Xiao-Yang; Lu, Lu; Qiu, Jiayin; Zou, Peng; Yu, Fei; Jiang, Xing-Kai; Li, Lin; Jiang, Shibo; Liu, Shuwen; Xie, Lan published the artcile< Small molecule fusion inhibitors: Design, synthesis and biological evaluation of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives targeting HIV-1 gp41>, Reference of 10574-69-3, the main research area is benzyloxothioxothiazolidinylidenemethyl carboxyhydroxyphenyl dimethylpyrrole preparation antiaids AIDS HIV fusion inhibitor; 3-Substituted N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole derivatives; Anti-HIV agents; HIV-1 gp41; Small-molecule fusion inhibitors.

By a scaffold elongation strategy, a series of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles I [R = Ph, 4-BrC6H4, 4-MeOC6H4, etc.; X = (CH2)n; n = 0-2] and related derivatives with a linear multiarom.-ring skeleton were designed, synthesized, and evaluated in HIV-1 gp41 and cellular assays. the most active compounds I [R = 4-MeO2CC6H4; 4-tBuC6H4; 3-MeO2CC6H4; X = CH2] exhibited very promising inhibitory potency with IC50 values of 1.8-2.6 μM and EC50 values of 0.3-1.5 μM against gp41 6-HB formation and HIV-1 replication in MT-2 cells, resp. Addnl., they were almost equally effective against both T20-sensitive and resistant strains. The related SAR studies and mol. modeling results provided potential for further developing a new class of nonpeptide small mol. fusion inhibitors targeting the HIV-1 gp41.

Bioorganic & Medicinal Chemistry published new progress about AIDS (disease). 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Reference of 10574-69-3.

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