Category: 64559-06-4

Tong, Wei published the artcilePalladium-Metalated Porous Organic Polymers as Recyclable Catalysts for the Chemoselective Synthesis of Thiazoles from Thiobenzamides and Isonitriles, Related Products of amides-buliding-blocks, the publication is Organic Letters (2018), 20(8), 2494-2498, database is CAplus and MEDLINE.

Two types of thiazole derivatives are synthesized through a multistep cascade sequence with Pd-metalated phosphorus-doped porous organic polymers (POPs) as heterogeneous catalysts. The POPs could be used as both ligands and catalyst supports. No obvious aggregation and loss of any catalytic activity of the catalysts were observed after 10 runs of the reaction. More importantly, imidazo[4,5-d]thiazoles, which are a new class of thiazole derivatives, could be obtained through K₂CO₃-promoted intramol. cyclization of the synthesized polysubstituted thiazoles. Furthermore, the in vitro anticancer activity of these new compounds were tested with MTT assay, and compound I exhibited good antitumor activity toward T-24 and A549 cells with IC₅₀ values of 10.3 ± 0.8 and 11.8 ± 0.5 μM, resp. In addition, the action mechanism of compound I on tumor cells was determined

Organic Letters published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C11H15NOS, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wang, Yu-Hao published the artcilePhosphine-Catalyzed Annulations Based on [3+3] and [3+2] Trapping of Ketene Intermediates with Thioamides, Formula: C8H9NOS, the publication is Organic Letters (2021), 23(21), 8147-8152, database is CAplus and MEDLINE.

A novel annulation via ketene intermediates, allenyl imide I and alkynoates RC₆H₄CCC(O)OC₆H₄-4-NO₂ (R = H, 4-MeC₆H₄, 2-ClC₆H₄, 3-BrC₆H₄, 4-FC₆H₄, 4-ClC₆H₄) bearing good leaving groups is used for their function in a tandem conjugate addition-elimination reaction (SN2′ type) promoted by nucleophilic phosphine catalysts and developed. By utilizing thioamides as R¹C(S)NH₂ (R¹ = 4-chlorophenyl, thiophen-2-yl, naphthalen-2-yl, etc.) 1S,3N-bis-nucleophiles, [3+3] and [3+2] annulations have been established to allow rapid access to 1,3-thiazin-4-ones II and 5-alkenyl thiazolones III in high yields, resp. Furthermore, the possible reaction mechanisms are proposed on the basis of deuterium labeling experiments and d. functional theory calculations

Organic Letters published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C13H16O2, Formula: C8H9NOS.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zeng, Hongyun published the artcileMethod for synthesis of 2,5-diaryl substituted thiazoles, Recommanded Product: 3-Methoxybenzothioamide, the publication is Youji Huaxue (2020), 40(8), 2535-2542, database is CAplus.

Thiazole ring is an important five-membered aromatic heterocyclic ring, and its derivatives have various biol. activities and are widely used in medicine. The synthesis of 2,5-diarylthiazole derivatives by acylation, thiolation, cyclization and Heck reaction using inexpensive and readily available substituted benzoic acid as raw materials was developed. The key point was to optimize the Heck reaction conditions and explore the possible reaction mechanism. The method has mild reaction conditions, simple operation, and good substrate universality, which provides a new direction for the synthesis of 2,5-diaryl substituted thiazoles.

Youji Huaxue published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C6H12N2O, Recommanded Product: 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Zhuo, Liang published the artcileAerobic Visible-Light Induced Intermolecular S-N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions, Safety of 3-Methoxybenzothioamide, the publication is European Journal of Organic Chemistry (2021), 2021(23), 3398-3402, database is CAplus.

Aerobic visible-light induced intermol. S-N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles I (R = Ph, 4-methoxyphenyl, thiophen-3-yl, etc.; R¹ = 4-methoxyphenyl, 2,6-dimethylphenyl, thiophen-2-yl, etc.) can be obtained from thioamides R/R¹C(S)NH₂. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S-N bonds.

European Journal of Organic Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C15H24O2, Safety of 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Protopopov, Mykola V. published the artcileIdentification of 1,3-thiazole-5-carboxylic Acid Derivatives as Inhibitors of Protein Kinase CK2, Name: 3-Methoxybenzothioamide, the publication is Current Enzyme Inhibition (2018), 14(2), 152-159, database is CAplus.

Serine/threonine protein kinase CK2 is involved in the regulation of a number of cellular functions such as cell growth, proliferation, differentiation and apoptosis. Increased activity of CK2 is associated with the development of different types of cancer, inflammatory response, pain and virus infections. Therefore, protein kinase CK2 is an attractive mol. target for the development of small-mol. inhibitors which can be important compounds for pharmaceutical application. The main aim of this research is to identify novel chem. class of CK2 inhibitors with good lead-like properties. In order to find novel CK2 inhibitors, virtual screening experiments were performed using Autodock software. Best-scored compounds were tested in vitro using P32 radioactive kinase assay. Small-mol. inhibitors of protein kinase CK2 were identified among the derivatives of 1,3-thiazole-5-carboxylic acid. The most active compound inhibited CK2 with IC₅₀ value of 0.4 μM. Ligand efficiency for studied derivatives of 1,3-thiazole-5-carboxylic acid was in the range from 0.45 to 0.56 kcal/mol/non-hydrogen atom. Considering the fact that the lower limit for ligand efficiency parameter is 0.3, the identified CK2 inhibitors among the derivatives of 1,3-thiazole-5-carboxylic acid are excellent candidates for further lead optimization.

Current Enzyme Inhibition published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Name: 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bianchini, Gianluca published the artcileDiscovery of Novel TRPM8 Blockers Suitable for the Treatment of Somatic and Ocular Painful Conditions: A Journey through pK_a and LogD Modulation, Name: 3-Methoxybenzothioamide, the publication is Journal of Medicinal Chemistry (2021), 64(22), 16820-16837, database is CAplus and MEDLINE.

Transient receptor potential melastatin 8 (TRPM8) is crucially involved in pain modulation and perception, and TRPM8 antagonists have been proposed as potential therapeutic approaches for pain treatment. Previously, we developed two TRPM8 antagonists and proposed them as drug candidates for topical and systemic pain treatment. Here, we describe the design and synthesis of these two TRPM8 antagonists (27 (I) and 45 (II)) and the rational approach of modulation/replacement of bioisosteric chem. groups, which allowed us to identify a combination of narrow ranges of pK_a and LogD values that were crucial to ultimately optimize their potency and metabolic stability. Following the same approach, we then pursued the development of new TRPM8 antagonists suitable for the topical treatment of ocular painful conditions and identified two new compounds (51 (III) and 59 (IV)), N-alkoxy amide derivatives, that can permeate across ocular tissue and reduce the behavioral responses induced by the topical ocular menthol challenge in vivo.

Journal of Medicinal Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Name: 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Orr, David published the artcileSingle-Step Microwave-Mediated Syntheses of Oxazoles and Thiazoles from 3-Oxetanone: A Synthetic and Computational Study, Recommanded Product: 3-Methoxybenzothioamide, the publication is Chemistry – A European Journal (2013), 19(29), 9655-9662, database is CAplus and MEDLINE.

The direct microwave-mediated condensation between 3-oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further elaboration. Electronic structure calculations have shown that the order of events involves chalcogen atom attack at sp³ carbon and alkyl-oxygen cleavage. The critical role of acid catalysis was shown clearly, and the importance of acid strength was demonstrated. The calculated barriers were also fully consistent with the observed order of thioamide and amide reactivity. Spontaneous ring opening involves a modest degree of C-O cleavage, moderating the extent of strain relief. On the acid-catalyzed pathway, C-O cleavage is less extensive still, but proton transfer to the nucleofuge is well advanced with the carboxylic acid catalysts, and essentially complete with methanesulfonic acid.

Chemistry – A European Journal published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Recommanded Product: 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Walczynski, K. published the artcileHistamine H₁ receptor ligands. Part I. Novel thiazol-4-ylethanamine derivatives: synthesis and in vitro pharmacology, Recommanded Product: 3-Methoxybenzothioamide, the publication is Farmaco (1999), 54(8), 533-541, database is CAplus and MEDLINE.

A series of 2-substituted thiazol-4-ylethanamines have been synthesized and tested for their histaminergic H₁-receptor activities. The compounds with 2-Ph substitution, regardless of the different physicochem. properties of the meta-substituents at the Ph ring, showed weak H₁-agonistic activity with pD₂ values ranging from 4.35 to 5.36. When the Ph group was replaced by a benzyl group, the resulting compounds all exhibited weak H₁-antagonistic activity (pA₂: 4.14-4.82).

Farmaco published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C10H9NO4S, Recommanded Product: 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Oda, Kazuaki published the artcilePhotochemistry of the nitrogen-thiocarbonyl systems. 30. Intermolecular photoaddition reaction of arenecarbothioamides to 2-methoxy- and 2-(trimethylsiloxy)furans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation, Safety of 3-Methoxybenzothioamide, the publication is Chemical & Pharmaceutical Bulletin (1997), 45(4), 584-589, database is CAplus.

Irradiation of arenecarbothioamides, e.g., 3-RC₆H₄C(S)NH₂ (R = H, Me, OMe, cyano, NO₂), with 2-methoxyfuran in benzene solution gave arene-fused aminobenzoates, e.g., I, in moderate yields accompanied by small amounts of arylpyrroles or arylthiophenes. In the case of 2-(trimethylsiloxy)furan, arenecarbothioamides gave arene-fused aminobenzoates in good yields as sole products. It was demonstrated that certain furan derivatives are potentially useful as building blocks in photoinduced benzannulation.

Chemical & Pharmaceutical Bulletin published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Safety of 3-Methoxybenzothioamide.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Brownlee, R. T. C. published the artcileNatural abundance nitrogen-15 chemical shifts in substituted benzamides and thiobenzamides, Formula: C8H9NOS, the publication is Magnetic Resonance in Chemistry (1986), 24(9), 821-6, database is CAplus.

¹⁵N substituent chem. shifts (measured at natural abundance at 0.4 M concentration) and calculated (ab initio, STO-3G) electron densities at the N and O (or S) are reported for series of para- and meta-substituted benzamides and thiobenzamides with NMe₂, NH₂, OMe, NHCOMe, F, Cl, Br, I, Me, H, COMe, CO₂Me, CF₃, CN, NO₂, CONH₂ and CSNH₂ substituents. The ¹⁵N shifts are very sensitive to the substituent effects. The dual substituent parameter method shows excellent correlations of ¹⁵N shifts against substituent field and resonance effects, with the sensitivity in the thiobenzamides being double that in the benzamides. In contrast, calculated π-electron densities at the N show the same sensitivity to substituents in both series. The ¹⁵N shifts correlate well with the calculated π-electron densities at the N; however, estimates of the shielding based on local electron densities (described in Pople’s independent electron model) cannot account for the increased sensitivity to the substituent effects observed for ¹⁵N chem. shifts of thiobenzamides. It is suggested that nonlocal shielding from S and O are responsible for the chem. shift trends.

Magnetic Resonance in Chemistry published new progress about 64559-06-4. 64559-06-4 belongs to amides-buliding-blocks, auxiliary class Amine,Benzene,Amide,Ether, name is 3-Methoxybenzothioamide, and the molecular formula is C8H9NOS, Formula: C8H9NOS.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics