Tag: M.W=100-150

Stachulski, Andrew V.; Pidathala, Chandrakala; Row, Eleanor C.; Sharma, Raman; Berry, Neil G.; Iqbal, Mazhar; Bentley, Joanne; Allman, Sarah A.; Edwards, Geoffrey; Helm, Alison; Hellier, Jennifer; Korba, Brent E.; Semple, J. Edward; Rossignol, Jean-Francois published the artcile< Thiazolides as Novel Antiviral Agents. 1. Inhibition of Hepatitis B Virus Replication>, Formula: C6H10N2S, the main research area is thiazolide preparation Hepatitis replication inhibition antiviral human structure activity.

The syntheses and activities of a wide range of thiazolides [viz., 2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis B virus replication, with results of QSAR anal. are reported. The prototypical thiazolide, nitazoxanide [2-hydroxybenzoyl-N-(5-nitrothiazol-2-yl)amide, NTZ] I, is a broad spectrum antiinfective agent effective against anaerobic bacteria, viruses, and parasites. By contrast, 2-hydroxybenzoyl-N-(5-chlorothiazol-2-yl)amide II is a novel, potent, and selective inhibitor of hepatitis B replication (EC50 = 0.33 μm) but is inactive against anaerobes. Several 4′- and 5′-substituted thiazolides show good activity against HBV; by contrast, some related salicyloylanilides show a narrower spectrum of activity. The ADME properties of II are similar to I, viz., the O-acetate is an effective prodrug, and the O-aryl glucuronide is a major metabolite. The QSAR study shows a good correlation of observed EC90 for intracellular virions with thiazolide structural parameters. Finally the mechanism of action of thiazolides in relation to the present results is discussed.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Formula: C6H10N2S.

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

Ching, Kuan-Chieh; Tran, Thi Ngoc Quy; Amrun, Siti Naqiah; Kam, Yiu-Wing; Ng, Lisa F. P.; Chai, Christina L. L. published the artcile< Structural Optimizations of Thieno[3,2-b]pyrrole Derivatives for the Development of Metabolically Stable Inhibitors of Chikungunya Virus>, Quality Control of 1003-32-3, the main research area is thieno pyrrole derivative preparation metabolic stability Chikungunya Virus antiviral.

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus, and there is no approved effective antiviral treatment currently available for CHIKV. We previously reported the discovery of thieno[3,2-b]pyrrole 1b that displayed good antiviral activity against CHIKV infection in vitro. However, it has a short half-life in the presence of human liver microsomes (HLMs) (T1/2 = 2.91 min). Herein, we report further optimization studies in which potential metabolically labile sites on compound 1b were removed or modified, resulting in the identification of thieno[3,2-b]pyrrole 20 and pyrrolo[2,3-d]thiazole 23c possessing up to 17-fold increase in metabolic half-lives in HLMs and good in vivo pharmacokinetic properties. Compound 20 not only attenuated viral RNA production and displayed broad-spectrum antiviral activity against other alphaviruses and CHIKV isolates but also exhibited limited cytotoxic liability (CC50 > 100 μM). These studies have identified two compounds that have the potential for further development as antiviral drugs against CHIKV infection.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Quality Control of 1003-32-3.

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

Sparey, Tim; Abeywickrema, Pravien; Almond, Sarah; Brandon, Nick; Byrne, Noel; Campbell, Alister; Hutson, Pete H.; Jacobson, Marlene; Jones, Brian; Munshi, Sanjeev; Pascarella, Danette; Pike, Andrew; Prasad, G. Sridhar; Sachs, Nancy; Sakatis, Melanie; Sardana, Vinod; Venkatraman, Shankar; Young, Mary Beth published the artcile< The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors>, Electric Literature of 1003-32-3, the main research area is fused pyrrole carboxylate preparation aminoacid oxidase DAO inhibitor structure; schizophrenia fused pyrrole carboxylic acid DAO inhibitor.

The NMDA hypofunction hypothesis of schizophrenia’ can be tested in a number of ways. DAO is the enzyme primarily responsible for the metabolism of D-serine, a co-agonist for the NMDA receptor. We identified novel DAO inhibitors, in particular, acid 1, which demonstrated moderate potency for DAO in vitro and ex vivo, and raised plasma D-serine levels after dosing i.p. to rats. In parallel, analogs were prepared to survey the SARs of 1.

Bioorganic & Medicinal Chemistry Letters published new progress about Antipsychotics. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Electric Literature of 1003-32-3.

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

Siegel, David J.; Anderson, Grace I.; Paul, Lauren M.; Seibert, Philipp J.; Hillesheim, Patrick C.; Sheng, Yinghong; Zeller, Matthias; Taubert, Andreas; Werner, Peter; Balischewski, Christian; Michael, Scott F.; Mirjafari, Arsalan published the artcile< Design Principles of Lipid-like Ionic Liquids for Gene Delivery>, Recommanded Product: 4,5-Dihydrothiazole-2-thiol, the main research area is ionic liquid gene delivery amphiphile lipid; DNA delivery; biomaterials; cationic lipids; gene therapy; ionic liquids; lipid-like materials; nonviral vectors.

We developed lipid-like ionic liquids, containing 2-mercaptoimidazolium and 2-mercaptothiazolinium headgroups tethered to two long saturated alkyl chains, as carriers for in vitro delivery of plasmid HEK DNA into 293T cells. We employed a combination of modular design, synthesis, X-ray anal., and computational modeling to rationalize the self-assembly and desired physicochem. and biol. properties. The results suggest that thioamide-derived ionic liquids may serve as a modular platform for lipid-mediated gene delivery. This work represents a step toward understanding the structure-function relationships of these amphiphiles with long-range ordering and offering insight into design principles for synthetic vectors based on self-assembly behavior.

ACS Applied Bio Materials published new progress about Amphiphiles. 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

Fushimi, Makoto; Buck, Hannes; Balbach, Melanie; Gorovyy, Anna; Ferreira, Jacob; Rossetti, Thomas; Kaur, Navpreet; Levin, Lonny R.; Buck, Jochen; Quast, Jonathan; van den Heuvel, Joop; Steegborn, Clemens; Finkin-Groner, Efrat; Kargman, Stacia; Michino, Mayako; Foley, Michael A.; Miller, Michael; Liverton, Nigel J.; Huggins, David J.; Meinke, Peter T. published the artcile< Discovery of TDI-10229: A Potent and Orally Bioavailable Inhibitor of Soluble Adenylyl Cyclase (sAC, ADCY10)>, Computed Properties of 1003-32-3, the main research area is adenylyl cyclase inhibitor oral bioavailability.

Soluble adenylyl cyclase (sAC) has gained attention as a potential therapeutic target given the role of this enzyme in intracellular signaling. We describe successful efforts to design improved sAC inhibitors amenable for in vivo interrogation of sAC inhibition to assess its potential therapeutic applications. This work culminated in the identification of TDI-10229 (12), which displays nanomolar inhibition of sAC in both biochem. and cellular assays and exhibits mouse pharmacokinetic properties sufficient to warrant its use as an in vivo tool compound

ACS Medicinal Chemistry Letters published new progress about Drug design. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Computed Properties of 1003-32-3.

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

Kim, Ho Shin; Hammill, Jared T.; Scott, Daniel C.; Chen, Yizhe; Rice, Amy L.; Pistel, William; Singh, Bhuvanesh; Schulman, Brenda A.; Guy, R. Kiplin published the artcile< Improvement of Oral Bioavailability of Pyrazolo-Pyridone Inhibitors of the Interaction of DCN1/2 and UBE2M>, Formula: C4H3NOS, the main research area is carcinoma DCN1 UBE2M interaction inhibitors NEDD8 pharmacokinetic oral bioavailability.

The cullin-RING ubiquitin ligases (CRLs) are ubiquitin E3 enzymes that play a key role in controlling proteasomal degradation and are activated by neddylation. We previously reported inhibitors that target CRL activation by disrupting the interaction of defective in cullin neddylation 1 (DCN1), a CRL neddylation co-E3, and UBE2M, a neddylation E2. Our first-generation inhibitors possessed poor oral bioavailability and fairly rapid clearance that hindered the study of acute inhibition of DCN-controlled CRL activity in vivo. Herein, we report studies to improve the pharmacokinetic performance of the pyrazolo-pyridone inhibitors. The current best inhibitor, 40 (I), inhibits the interaction of DCN1 and UBE2M, blocks NEDD8 transfer in biochem. assays, thermally stabilizes cellular DCN1, and inhibits anchorage-independent growth in a DCN1 amplified squamous cell carcinoma cell line. Addnl., we demonstrate that a single oral 50 mg/kg dose sustains plasma exposures above the biochem. IC90 for 24 h in mice.

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

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

Lam, P. Y. S.; Deudon, S.; Hauptman, E.; Clark, C. G. published the artcile< α-Nitrogen-activating effect in the room temperature copper-promoted N-arylation of heteroaryl carboxamides with phenylsiloxane or 4-tolylboronic acid>, Product Details of C5H6N2OS, the main research area is nitrogen heteroaromatic carboxamide phenylsiloxane arylation; tolylboronate nitrogen heteroaromatic carboxamide arylation; cross coupling nitrogen heteroaromatic carboxamide phenylsiloxane.

α-N-containing heteroaryl carboxamides undergo Cu-promoted N-phenylation with hypervalent PhSi(OMe)3 at room temperature, in the absence of base and in air. Arylboronic acid can substitute for PhSi(OMe)3 as the organometalloid. The α-heteroatom chelating effect is in the decreasing order of N > O, S. This discovery opens up the possibility of using other α-N functional groups to direct the N-arylation of peptides and simple amides under conditions as mild as that of amide bond formation.

Tetrahedron Letters published new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (heteroaromatic). 31825-95-3 belongs to class thiazole, and the molecular formula is C5H6N2OS, Product Details of C5H6N2OS.

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

Zhao, Mengzhen; Xiang, Yao; Jiao, Xuping; Cao, Bo; Tang, Shoufeng; Zheng, Ziye; Zhang, Xiaoyu; Jiao, Tifeng; Yuan, Deling published the artcile< MoS2 co-catalysis promoted CaO2 Fenton-like process: Performance and mechanism>, Application of C3H5NS2, the main research area is rhodamine molybdenum sulfide catalyst calcium peroxide Fenton reaction.

Fenton reaction is widely applied to treat organic contaminant through hydroxyl radicals (HO·), which is formed from the catalytic reaction of hydrogen peroxide (H2O2) and Fe2+. Nevertheless, its well application for actual wastewater has been confined by the narrow range of pH, disproportionation of H2O2 and inefficiency of Fe2+/Fe3+ circulation. To overcome these shortcomings, an improved Fenton-like method applying calcium peroxide (CaO2) as the substitution of H2O2 and molybdenum disulfide (MoS2) as the co-catalyst was proposed. The results indicated the efficient rhodamine B (RhB) removal (98.6%) was achieved under the conditions of 1 mmol L-1 CaO2, 0.5 mmol L-1 Fe2+, 0.3 g L-1 MoS2, and initial pH 5.85 within 5 min, and this system could well degrade other dyes, antibiotic, and phenol. The MoS2 addition could promote the Fe2+/Fe3+ conversion and H2O2 disintegration. The radical masking tests and ESR demonstrated that the HO· was the main active substances during this process. The decomposition intermediates of RhB were identified through the mass spectra anal., and their ecotoxicities were assessed by the toxicity estimation software. Finally, this process also presented a favorable performance for the real wastewater treatment, which is a potential route to promote the development of Fenton method.

Separation and Purification Technology published new progress about Bioaccumulation. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Application of C3H5NS2.

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

Kang, Taeho; Erbay, Tugce G.; Xu, Kane L.; Gallego, Gary M.; Burtea, Alexander; Nair, Sajiv K.; Patman, Ryan L.; Zhou, Ru; Sutton, Scott C.; McAlpine, Indrawan J.; Liu, Peng; Engle, Keary M. published the artcile< Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds>, Category: thiazole, the main research area is copper catalyzed hydroboration benzylidenecyclobutane diborane kinetics; chloro copper bisphosphinobenzene complex preparation crystal structure; mol structure chloro copper bisphosphinobenzene complex; 4-membered rings; Copper catalysis; benzylidenecyclobutanes; heterocycle; hydroborations; modified dppbz ligands; tertiary boronic esters.

A unified synthetic strategy to access tertiary four-membered carbo/heterocyclic boronic esters is reported. The use of a Cu(I) catalyst in combination with a modified 1,2-bis(diphenylphosphino)benzene (dppbz) ligand enables regioselective hydroboration of various trisubstituted benzylidenecyclobutanes and carbo/heterocyclic analogs. The reaction conditions are mild, and the method tolerates a wide range of medicinally relevant heteroarenes. The protocol can be conveniently conducted on a gram scale, and the tertiary boronic ester products undergo facile diversification into valuable targets. Reaction kinetics and computational studies indicate that the migratory insertion step is turnover-limiting and accelerated by electron-withdrawing groups on the dppbz ligand. Energy decomposition anal. calculations reveal that electron-deficient P-aryl groups on the dppbz ligand enhance the T-shaped π/π interactions with the substrate and stabilize the migratory insertion transition state.

ACS Catalysis published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation) (benzylcyclobutane heteroarenes). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Category: thiazole.

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

Gwaltney, Stephen L.; O’Connor, Stephen J.; Nelson, Lissa T. J.; Sullivan, Gerard M.; Imade, Hovis; Wang, Weibo; Hasvold, Lisa; Li, Qun; Cohen, Jerome; Gu, Wen-Zhen; Tahir, Stephen K.; Bauch, Joy; Marsh, Kennan; Ng, Shi-Chung; Frost, David J.; Zhang, Haiying; Muchmore, Steve; Jakob, Clarissa G.; Stoll, Vincent; Hutchins, Charles; Rosenberg, Saul H.; Sham, Hing L. published the artcile< Aryl tetrahydropyridine inhibitors of farnesyltransferase: glycine, phenylalanine and histidine derivatives>, Quality Control of 1003-32-3, the main research area is glycine phenylalanine histidine derivative synthesis antitumor agent farnesyltransferase inhibitor; aryl tetrahydropyridine inhibitor farnesyltransferase antitumor structure activity; antitumor agent histidine methionine derivative crystal structure.

Inhibitors of farnesyltransferase are effective against a variety of tumors in mouse models of cancer. Clin. trials to evaluate these agents in humans are ongoing. In our effort to develop new farnesyltransferase inhibitors, we have discovered a series of aryl tetrahydropyridines that incorporate substituted glycine, phenylalanine and histidine residues. The design, synthesis, SAR and biol. properties of these compounds will be discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about Amino acids Role: BSU (Biological Study, Unclassified), PAC (Pharmacological Activity), PKT (Pharmacokinetics), PRP (Properties), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), PREP (Preparation), USES (Uses). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Quality Control of 1003-32-3.

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