Tag: M.W=100-150

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

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

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

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

Ryu, Se Hwan; Ra, Jongmin; Ko, Haye Min published the artcile< Efficient Synthesis of Sulfenamides through Mitsunobu-type Coupling Reaction of Thiols with Amines using Dibenzyl Azodicarboxylate>, Quality Control of 96-53-7, the main research area is sulfenamide preparation; thiol amine Mitsunobu coupling; disulfides preparation.

S-H activation reaction of thiols employing dibenzyl azodicarboxylate (DBAD) had been developed for the preparation of sulfenamides I [R = H; R1 = Et, Bn, cyclopropyl, cyclopentyl, cyclohexyl; RR1 = (CH2)4, (CH2)6, (CH2)2O(CH2)2, etc.; X = O, S]. The dehydrogenation of thiols and amines under these reaction conditions involved the formation of dibenzyl hydrazine-1,2-dicarboxylate, which led to the S-N bond formation reaction. The reaction proceeded efficiently with release of dibenzyl hydrazine-1,2-dicarboxylate and afforded various sulfenamides I in good to excellent yields.

Asian Journal of Organic Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Quality Control of 96-53-7.

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

Kirubakaran, Sivapriya; Gorla, Suresh Kumar; Sharling, Lisa; Zhang, Minjia; Liu, Xiaoping; Ray, Soumya S.; MacPherson, Iain S.; Striepen, Boris; Hedstrom, Lizbeth; Cuny, Gregory D. published the artcile< Structure-activity relationship study of selective benzimidazole-based inhibitors of Cryptosporidium parvum IMPDH>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is benzimidazole inhibitor Cryptosporidium parvum IMPDH preparation SAR antiparasitic activity.

Cryptosporidium parasites are important waterborne pathogens of both humans and animals. The Cryptosporidium parvum and Cryptosporidium hominis genomes indicate that the only route to guanine nucleotides is via IMP dehydrogenase (IMPDH). Thus the inhibition of the parasite IMPDH presents a potential strategy for treating Cryptosporidium infections. A selective benzimidazole-based inhibitor of C. parvum IMPDH (CpIMPDH) was previously identified in a high throughput screen. Herein is reported a structure-activity relationship study of benzimidazole-based compounds that resulted in potent and selective inhibitors of CpIMPDH. Several compounds display potent antiparasitic activity in vitro.

Bioorganic & Medicinal Chemistry Letters published new progress about Cryptosporidiosis. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Recommanded Product: Thiazole-5-carboxyaldehyde.

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

Wang, Jing; Liang, Jing; Liu, Xu; Xiao, Han; Dong, Fuping; Wang, Yilin; Shu, Xin; Huang, Furong; Liu, Hai-Bo published the artcile< Thiazoline-pyrene selective and sensitive fluorescence ""turn-on"" sensor for detection of Cu2+>, Recommanded Product: 4,5-Dihydrothiazole-2-thiol, the main research area is thiazoline pyrene selective sensitive fluorescence sensor copper detection; Cu2+ detection; Fluorescence; Pyrene; Thiazoline; “Turn-on” sensor.

A thiazoline and pyrene containing sensor 1 (I) was synthesized via 1-pot reaction and used as a highly selective and sensitive fluorescence turn-on sensor for Cu2+ detection, via the fluorescence enhancement of pyrene monomer emission. The 2:1 stoichiometry of 1 and Cu2+ was calculated from Job’s plots based on fluorescent titrations, and the complexation of 1 with Cu2+ was also supported by mass spectra, FTIR spectra, 1H NMR spectra and d. functional theory anal. The fluorescence intensity of 1 at 389 nm and 410 nm increased significantly upon the addition of Cu2+. Limit of detection and association constant value of 1-Cu2+ were calculated using standard deviations and linear fittings, resp. 1 Was active for Cu2+ detection in the wide pH range of 2.0-11.0.

Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about Colorimetry. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Recommanded Product: 4,5-Dihydrothiazole-2-thiol.

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

Wang, Gang; Xin, Xiaodong; Wang, Zehua; Lu, Gang; Ma, Yudao; Liu, Lei published the artcile< Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives>, Electric Literature of 96-53-7, the main research area is ether azolidinyl alkanone preparation regioselective enantioselective cross dehydrogenative coupling.

A formal catalytic enantioselective cross-dehydrogenative coupling of saturated ethers with diverse carboxylic acid derivatives involving an initial oxidative acetal formation, followed by nickel(II)-catalyzed asym. alkylation. The one-pot, general and modular method exhibited wide compatibility of a broad range of saturated ethers not only including prevalent THF and tetrahydropyran but also including medium- and large-sized cyclic moieties and acyclic ones with excellent enantioselectivity and functional group tolerance. The application in the rapid preparation of biol. active mols. that are difficult to access with existing methods was also demonstrated.

Nature Communications published new progress about Aliphatic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Hagen, Susan E.; Domagala, John; Gajda, Christopher; Lovdahl, Michael; Tait, Bradley D.; Wise, Eric; Holler, Tod; Hupe, Donald; Nouhan, Carolyn; Urumov, Andrej; Zeikus, Greg; Zeikus, Eric; Lunney, Elizabeth A.; Pavlovsky, Alexander; Gracheck, Stephen J.; Saunders, James; VanderRoest, Steve; Brodfuehrer, Joanne published the artcile< 4-Hydroxy-5,6-dihydropyrones as inhibitors of HIV protease: the effect of heterocyclic substituents at C-6 on antiviral potency and pharmacokinetic parameters>, Category: thiazole, the main research area is hydroxydihydropyrone HIV protease inhibitor antiviral agent.

Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, the authors previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable back-up candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocycle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymic and cellular tests) and low cellular toxicity; furthermore, several analogs exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailability was (S)-3-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (I). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, I was chosen for further preclin. evaluation.

Journal of Medicinal Chemistry published new progress about Anti-HIV agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Category: thiazole.

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

Huang, Zhi-Xing; Yu, Jia-Hui; Xu, Xing-Jun; Xu, Xiao-Fang; Zeng, Ting; Lin, Jing; Chen, Wei-Min published the artcile< Cajaninstilbene acid analogues as novel quorum sensing and biofilm inhibitors of Pseudomonas aeruginosa>, HPLC of Formula: 1003-32-3, the main research area is Pseudomonas aeruginosa Cajaninstilbene acid analog quorum sensing biofilm inhibitor; Anti-Biofilm; Cajaninstilbene acid; Pseudomonas aeruginosa; Quorum sensing regulator.

Biofilm formation and virulence factor secretion in opportunistic pathogen Pseudomonas aeruginosa are essential for establishment of chronic and recurrent infection, which are regulated by quorum sensing (QS) system. In this study, a set of cajaninstilbene acid analogs were designed and synthesized, and their abilities to inhibit QS and biofilm formation were investigated. Among all the compounds, compounds 3g, 3m and 3o showed potent anti-biofilm activity, especially 3o exhibited promising biofilm inhibitory activity with biofilm inhibition ratio of 49.50 ± 1.35% at 50 μM. Three lacZ reporter strains were constructed to identify the effects of compound 3o on different QS systems. Compound 3o showed the suppression on the expression of lasB-lacZ and pqsA-lacZ as well as on the production of their corresponding virulence factors. Therefore, compound 3o is expected to be generated as a lead compound with inhibition of biofilm formation and QS of Pseudomonas aeruginosa.

Microbial Pathogenesis published new progress about Microbial gene, lacZ Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, HPLC of Formula: 1003-32-3.

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