Month: October 2022

Valente, Sergio; Mellini, Paolo; Spallotta, Francesco; Carafa, Vincenzo; Nebbioso, Angela; Polletta, Lucia; Carnevale, Ilaria; Saladini, Serena; Trisciuoglio, Daniela; Gabellini, Chiara; Tardugno, Maria; Zwergel, Clemens; Cencioni, Chiara; Atlante, Sandra; Moniot, Sebastien; Steegborn, Clemens; Budriesi, Roberta; Tafani, Marco; Del Bufalo, Donatella; Altucci, Lucia; Gaetano, Carlo; Mai, Antonello published the artcile< 1,4-Dihydropyridines Active on the SIRT1/AMPK Pathway Ameliorate Skin Repair and Mitochondrial Function and Exhibit Inhibition of Proliferation in Cancer Cells>, Computed Properties of 1003-32-3, the main research area is preparation dihydropyridine sirtuin AMPK antitumor neoplasm.

Modulators of sirtuins are considered promising therapeutic targets for the treatment of cancer, cardiovascular, metabolic, inflammatory, and neurodegenerative diseases. Here we prepared new 1,4-dihydropyridines (DHPs) bearing changes at the C2/C6, C3/C5, C4, or N1 position. Tested with the SIRTainty procedure, some of them displayed increased SIRT1 activation with respect to the prototype 3a, high NO release in HaCat cells, and ameliorated skin repair in a mouse model of wound healing. In C2C12 myoblasts, two of them improved mitochondrial d. and functions. All the effects were reverted by coadministration of compound C (9), an AMPK inhibitor, or of EX-527 (10), a SIRT1 inhibitor, highlighting the involvement of the SIRT1/AMPK pathway in the action of DHPs. Finally, tested in a panel of cancer cells, the water-soluble form of 3a, compound 8, displayed antiproliferative effects in the range of 8-35 μM and increased H4K16 deacetylation, suggesting a possible role for SIRT1 activators in cancer therapy.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 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

Aursnes, M.; Tungen, J. E.; Vik, A.; Dalli, J.; Hansen, T. V. published the artcile< Stereoselective synthesis of protectin D1: a potent anti-inflammatory and proresolving lipid mediator>, Related Products of 171877-39-7, 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, and the molecular formula is C10H11NS2, Related Products of 171877-39-7.

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

Moghimi, S.; Heravi, M. M.; Oskooie, H. A.; Beheshtiha, Y. S. published the artcile< A novel un-catalyzed and solvent-free method for the synthesis of 2-thioxothiazolidin-4-ones>, Category: thiazole, the main research area is rhodanine preparation catalyst solvent free; primary amine carbon disulfide chloroacetyl chloride multicomponent re??action.

An easy and highly efficient one-pot, three-component synthesis of rhodanines was reported. The reaction of primary amines, carbon disulfide and chloroacetyl chloride proceeded in the absence of solvent and catalyst affording 2-thioxothiazolidin-4-ones in good to excellent yields.

Scientia Iranica, Transaction C: Chemistry, Chemical Engineering published new progress about Primary amines Role: RCT (Reactant), RACT (Reactant or Reagent). 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Category: thiazole.

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

Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C. published the artcile< Regio- and stereoselective synthesis of 1,4-dihydropyridines by way of an intramolecular interaction of a thiocarbonyl or carbonyl with a pyridinium nucleus>, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione, the main research area is pyridine regioselective stereoselective preparation; thiocarbonyl interaction pyridinium; carbonyl interaction pyridinium; stereoselective regioselective nucleophilic addition acetal organometallic pyridinium salt; absolute configuration pyridine CD.

Chiral 1,4-dihydropyridines were prepared by the regio- and stereoselective addition of ketene silyl acetals and organometallic reagents to pyridinium salts. In the addition reaction, an intramol. interaction between the thiocarbonyl or carbonyl with the pyridinium nucleus plays an important role in bringing about the selectivities. The absolute configuration of the newly produced stereogenic center of the 1,4-dihydropyridines was determined by X-ray anal. and CD Cotton effects after conversion into the appropriate derivatives The working model for the stereoselectivity was proposed based on the ab initio calculations at the RHF/3-21G* level.

Tetrahedron published new progress about Absolute configuration. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Recommanded Product: (S)-4-Benzylthiazolidine-2-thione.

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

Hebade, Madhav J.; Kamble, Rahul D.; Hese, Shrikant V.; Mogle, Pratima P.; Ambhore, Ajay N.; Kadam, Shuddhodan N.; Dawane, Bhaskar S. published the artcile< A rapid, mild, and efficient method for C-5 iodination/thiocyanation of 2-aminothiazoles>, HPLC of Formula: 57493-24-0, the main research area is green multitasking substitution iodination thiocyanation aminothiazole; iodo aminothiazole green preparation iodination; thiocyano aminothiazole green preparation thiocyanation.

An efficient, green, rapid multitasking protocol for the selective C-5 substitution of 2-aminothiazole using iodic acid and aqueous PEG-400 was developed. The method found suitable for C-5 substitution i.e. iodination and thiocyanation of 2-amino thiazole using iodine and ammonium thiocyanate resp. Iodic acid was found to be a good oxidant and aqueous PEG-400 as green reaction solvent.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about Cyanation, thiocyanation. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, HPLC of Formula: 57493-24-0.

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

Ung, Alison T.; Pyne, Stephen G.; Skelton, Brian W.; White, Allan H. published the artcile< Asymmetric synthesis of (1R,2S,3R)-2-acetyl-5-(1,2,3,4-tetrahydroxybutyl)thiazole>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is asym synthesis acetyltetrahydroxybutylthiazole; thiazole acetyltetrahydroxybutyl asym synthesis.

A method for preparing the thiazole analog I of the biol. active compound (1R,2S,3R)-2-acetyl-4(5)-(1,2,3,4-tetrahydroxybutyl)imidazole is reported.

Tetrahedron published new progress about Stereoselective synthesis. 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

Floyd, David M.; Stein, Philip; Wang, Zheng; Liu, Jian; Castro, Steve; Clark, Julie A.; Connelly, Michele; Zhu, Fangyi; Holbrook, Gloria; Matheny, Amy; Sigal, Martina S.; Min, Jaeki; Dhinakaran, Rajkumar; Krishnan, Senthil; Bashyum, Sridevi; Knapp, Spencer; Guy, R. Kiplin published the artcile< Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides>, Synthetic Route of 1003-32-3, the main research area is tetrahydroisoquinolone carboxanilide preparation antimalarial structure activity.

Phenotypic whole-cell screening in erythrocytic co-cultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent anti-malarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure-activity studies revealed relationships between potency and modifications at N-2, C-3 and C-4. Careful structure-property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicol. effects, inherent in the more potent primary screening hits such as (I). Analogs (II) and (+)-SJ733 (13i), with structural modifications at each site, were shown to possess excellent anti-malarial activity in vivo. The (+)-(3S,4S) enantiomer of 13i and similar analogs were identified as the more potent. Based on these studies, the authors have selected (+)-13i for further study as a preclin. candidate.

Journal of Medicinal Chemistry published new progress about Antimalarials. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Synthetic Route of 1003-32-3.

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

Zhao, Shenghao; Pang, Kaining; Huang, Yaning; Xiao, Ning published the artcile< Special electrochemical behaviour of sodium thiazolinyl-dithiopropane sulphonate during microvia filling>, Electric Literature of 96-53-7, the main research area is sodium thiazolinyl dithiopropane sulfonate microvia filling.

In this work, galvanostatic measurements were employed to study the electrochem. behavior of thiazolinyl-dithiopropane sulfonate (SH110) in a copper plating process, which indicated that it had a critical concentration of 12.5 mg L-1. At this critical concentration, it would accelerate copper deposition at strong forced convection but inhibit copper deposition at weak forced convection. To get more insight into SH110, its potential decomposition products, 3-mercapto-1-propanesulfonate (MPS) and 2-thiazoline-2-thiol (H1), were also investigated. It was found that MPS always presented an acceleration effect with its concentration increasing, whereas H1, with a simple mol. structure, also had a critical concentration, which was 1.25 mg L-1. As expected, superfilling can be achieved by using H1 as the single additive. Finally, the interaction between SH110 and H1 was studied to prove the decomposition of SH110, as well as to illustrate its action mechanism.

Transactions of the IMF published new progress about Decomposition. 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

Owczarzak, Agata; Dutkiewicz, Zbigniew; Kurczab, Rafal; Pietrus, Wojciech; Kubicki, Maciej; Grzeskiewicz, Anita M. published the artcile< Role of Staple Molecules in the Formation of S···S Contact in Thioamides: Experimental Charge Density and Theoretical Studies>, Formula: C3H5NS2, the main research area is thioamide contact staple mol.

The reasons behind the formation of S···S contacts in thioamides, the most important compounds with terminal sulfur atoms, were investigated by means of exptl. charge d. studies and theor. calculations As this interaction is to some extent similar to the much better-known halogen bond, geometrical anal. was performed using previously determined halogen bond formation criteria. To investigate the most representative thioamides, three compounds, namely, 6-aminothiouracil hydrate (ATU·H2O, 1), imidazolinethione (IMT, 2) and thiazolidinethione (TT, 3), were selected. In all three structures, relatively short S···S contacts displaying different geometries were observed Furthermore, different symmetry elements (mirror plane in ATU, inversion center in TT, and translation in IMT) determined the mutual orientation of the sulfur atoms in contact. The structural anal. and calculations proved that the isolated S•••S dimers are unstable and that they are stabilized by “”staple”” mols., which are any mols. present in the crystal structure that interact with both mols. forming the S···S contact. Several types of staple mols. were identified, differing in the area of interaction with the S···S dimer mol. The anal. of the data in the Cambridge Structural Database showed that the staple structures can be found in 77% of all structures with short S···S contacts (shorter than 3.4 Å) and in more than half of the structures with the contacts within the van der Waals radius limit. The calculations show that the smaller the distance between sulfur atoms in the S···S dimer, the greater the amount of energy needed for dimer stabilization. Consequently, the presence of a staple is essential.

Crystal Growth & Design published new progress about Bader electron density. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Formula: C3H5NS2.

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

Kobayashi, Naotake; Sato, Norihito; Fujimura, Yuko; Kihara, Tsuyoshi; Sugita, Katsuji; Takahashi, Kouji; Koike, Katsumi; Sugawara, Tamio; Tada, Yukio; Nakai, Hiroshi; Yoshikawa, Takayoshi published the artcile< Discovery of the Orally Effective Thyrotropin-Releasing Hormone Mimetic: 1-{N-[(4S,5S)-(5-Methyl-2-oxooxazolidine-4-yl)carbonyl]-3-(thiazol-4-yl)-L-alanyl}-(2R)-2-methylpyrrolidine Trihydrate (Rovatirelin Hydrate)>, Computed Properties of 1003-32-3, the main research area is TRH mimetics rovatirelin hydrate synthesis brain disease crystal structure.

We have explored orally effective TSH-releasing hormone (TRH) mimetics showing oral bioavailability and brain penetration by SAR study on the basis of in vivo antagonistic activity on reserpine-induced hypothermia in mice. By primary screening of the synthesized TRH mimetics, we found a novel TRH mimetic: L-pyroglutamyl-[3-(thiazol-4-yl)-L-alanyl]-L-prolinamide with high central nervous system (CNS) effect compared to TRH as a lead compound Further SAR optimization studies of this lead compound led to discovery of a novel orally effective TRH mimetic: 1-{N-[(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)carbonyl]-3-(thiazol-4-yl)-L-alanyl}-(2R)-2 -methylpyrrolidine trihydrate (Rovatirelin Hydrate), which was selected as a candidate for clin. trials.

ACS Omega published new progress about Bioavailability. 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