Tag: 100-200

Synthesis of 5-arylthiazoles. Comparative study between Suzuki cross-coupling reaction and direct arylation was written by Primas, Nicolas;Bouillon, Alexandre;Lancelot, Jean-Charles;El-Kashef, Hussein;Rault, Sylvain. And the article was included in Tetrahedron in 2009.HPLC of Formula: 1826-13-7 This article mentions the following:

A facile synthetic route to the thiazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-arylthiazoles. A comparative study between Suzuki cross-coupling reactions and palladium-catalyzed C5-H direct arylation on thiazole ring was achieved. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7HPLC of Formula: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.HPLC of Formula: 1826-13-7

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

Copper-Catalyzed Dehydrogenative Cross-Coupling of Benzothiazoles with Thiazoles and Polyfluoroarene was written by Fan, Shilu;Chen, Zhao;Zhang, Xingang. And the article was included in Organic Letters in 2012.Computed Properties of C9H7NS This article mentions the following:

A copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene under mild reaction conditions is described. E.g., in presence of CuI, Ag₂CO₃, and t-BuOLi, cross-coupling reaction of benzothiazole and 4,5-dimethylthiazole gave 71% I and 14% of the benzothiazole homocoupling product. This protocol provides a straightforward and operationally simple method for the synthesis of the 2,2′-linkage of thiazoles and 2-polyfluoroarylthiazoles of interest in life and material sciences. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Computed Properties of C9H7NS

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

Design, synthesis and SAR of substituted indoles as selective TrkA inhibitors was written by Hurzy, Danielle M.;Henze, Darrell A.;Cabalu, Tamara D.;Narayan, Kartik;Heller, Amanda;Cooke, Andrew J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.COA of Formula: C4H6N2S This article mentions the following:

A series of substituted indoles were examined as selective inhibitors of tropomyosin-related kinase receptor A (TrkA), a therapeutic target for the treatment of pain. An SAR optimization campaign based on ALIS screening lead compound I is reported. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.COA of Formula: C4H6N2S

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

Structure-activity relationship of biakamide, selective growth inhibitors under nutrient-starved condition from marine sponge was written by Ishida, Ryosuke;Matsumoto, Hirokazu;Ichii, Sayaka;Kobayashi, Motomasa;Arai, Masayoshi;Kotoku, Naoyuki. And the article was included in Chemical & Pharmaceutical Bulletin in 2019.Recommanded Product: 55661-33-1 This article mentions the following:

The tumor microenvironment is considered as one of the important targets for anticancer drug discovery. In particular, nutrient deficiency may be observed in tumor microenvironment; biakamides A-D (1-4) isolated from marine sponge Petrosaspongia sp. as growth inhibitors against cancer cells adapted to glucose-deprived conditions have potential as new drugs and tools for elucidating adaptation mechanisms to these conditions. In this paper, we investigated structure-activity relationship (SAR) of biakamide to create easily accessible analog and gain insights about participation of the substructures to growth-inhibitory activity toward development of anticancer drug. This work revealed that 14,15-dinor-biakamide C (5), which is easily accessible, has similar activity to natural biakamide C (3). In addition, detailed SAR study showed the terminal acyl chain is important for interacting with target mol. and amide part including thiazole ring has acceptability to convert structures without losing activity. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Recommanded Product: 55661-33-1

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

Synthesis and evaluation of andrographolide derivatives as potent anti-osteoporosis agents in vitro and in vivo was written by Zhang, Songxuan;Zhang, Yuting;Fang, Yuying;Chen, Hao;Hao, Mengjiao;Tan, Qingyun;Hu, Chen;Zhou, Huihao;Xu, Jun;Gu, Qiong. And the article was included in European Journal of Medicinal Chemistry in 2021.Formula: C4H6N2S This article mentions the following:

In this work, we found that 14-deoxy-11,12-didehydroandrographolide, a derivative of andrographolide, had greatly reduced cytotoxicity compared with andrographolide and exhibited moderate anti-osteoclastogenesis activity. Thirty compounds were synthesized by introducing anti-osteoporosis chemotypes at C-19 of 14-deoxy-11,12-didehydroandrographolide. Six of them exhibited stronger inhibition of osteoclastogenesis than andrographolide. Of note, compound I displayed the most potent activity with IC₅₀ value of 0.35μM. The expression levels of osteoclast-specific genes such as TRAcP, CTSK, NFATc1, and MMP-9 were also decreased by I treatment. Furthermore, Western blot and immunofluorescence analyses demonstrated that I inhibited osteoclast differentiation through downregulation of RANKL-induced NF-κB signaling pathway. In an ovariectomized (OVX) female mice model, I significantly ameliorated bone loss. Therefore, I exhibited promising in vivo efficacy and low toxicity, indicating its therapeutic potential for the treatment of osteoporosis. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Formula: C4H6N2S

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

Discovery of Quinazolines as Histamine H₄ Receptor Inverse Agonists Using a Scaffold Hopping Approach was written by Smits, Rogier A.;de Esch, Iwan J. P.;Zuiderveld, Obbe P.;Broeker, Joachim;Sansuk, Kamonchanok;Guaita, Elena;Coruzzi, Gabriella;Adami, Maristella;Haaksma, Eric;Leurs, Rob. And the article was included in Journal of Medicinal Chemistry in 2008.Product Details of 55661-33-1 This article mentions the following:

From a series of small fragments that was designed to probe the histamine H₄ receptor (H₄R), we previously described quinoxaline-containing fragments that were grown into high affinity H₄R ligands in a process that was guided by pharmacophore modeling. With a scaffold hopping exercise and using the same in silico models, we now report the identification and optimization of a series of quinazoline-containing H₄R compounds This approach led to the discovery of 6-chloro-N-(furan-3-ylmethyl)2-(4-methylpiperazin-1-yl)quinazolin-4-amine (VUF10499, 54) and 6-chloro-2-(4-methylpiperazin-1-yl)-N-(thiophen-2-ylmethyl)quinazolin-4-amine (VUF10497, 55) as potent human H₄R inverse agonists (pK_i = 8.12 and 7.57, resp.). Interestingly, both compounds also possess considerable affinity for the human histamine H₁ receptor (H₁R) and therefore represent a novel class of dual action H₁R/H₄R ligands, a profile that potentially leads to added therapeutic benefit. Compounds from this novel series of quinazolines are antagonists at the rat H₄R and were found to possess anti-inflammatory properties in vivo in the rat. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Product Details of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Product Details of 55661-33-1

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

Aminopyrazolo[1,5-a]pyrimidines as potential inhibitors of Mycobacterium tuberculosis: Structure activity relationships and ADME characterization was written by Soares de Melo, Candice;Feng, Tzu-Shean;van der Westhuyzen, Renier;Gessner, Richard K.;Street, Leslie J.;Morgans, Garreth L.;Warner, Digby F.;Moosa, Atica;Naran, Krupa;Lawrence, Nina;Boshoff, Helena I. M.;Barry, Clifton E. III;Harris, C. John;Gordon, Richard;Chibale, Kelly. And the article was included in Bioorganic & Medicinal Chemistry in 2015.SDS of cas: 55661-33-1 This article mentions the following:

Whole-cell high-throughput screening of a diverse SoftFocus library against Mycobacterium tuberculosis (Mtb) generated a novel aminopyrazolo[1,5-a]pyrimidine hit series. The synthesis and structure activity relationship studies identified compounds with potent antimycobacterial activity. The SAR of over 140 compounds shows that the 2-pyridylmethylamine moiety at the C-7 position of the pyrazolopyrimidine scaffold was important for Mtb activity, whereas the C-3 position offered a higher degree of flexibility. The series was also profiled for in vitro cytotoxicity and microsomal metabolic stability as well as physicochem. properties. Consequently liabilities to be addressed in a future lead optimization campaign have been identified. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1SDS of cas: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.SDS of cas: 55661-33-1

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

Synthesis and Evaluation of Antibacterial Activity of Bottromycins was written by Yamada, Takeshi;Yagita, Miu;Kobayashi, Yutaka;Sennari, Goh;Shimamura, Hiroyuki;Matsui, Hidehito;Horimatsu, Yuki;Hanaki, Hideaki;Hirose, Tomoyasu;Omura, Satoshi;Sunazuka, Toshiaki. And the article was included in Journal of Organic Chemistry in 2018.Application of 55661-33-1 This article mentions the following:

Total synthesis of bottromycin A₂ can be accomplished through a diastereoselective Mannich reaction of a chiral sulfinamide, mercury-mediated intermol. amidination, and cyclization of a constrained tetracyclic peptide. Exploitation of this process allowed the synthesis of several novel bottromycin analogs. The antimicrobial activity of these analogs was evaluated in vitro against Gram-pos. bacteria, such as methicillin resistant Staphylococcus aureus (MRSA) and vancomycin resistant enterococci (VRE). Structure-activity relationships were explored taking into consideration the unique three-dimensional structure of the compounds Notably, one of the new analogs devoid of a Me ester, which is known to lower the in vivo efficacy of bottromycin, exhibited antibacterial bioactivity comparable to that of vancomycin. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Application of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application of 55661-33-1

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

Discovery of triazolone derivatives as novel, potent stearoyl-CoA desaturase-1 (SCD1) inhibitors was written by Sun, Shaoyi;Zhang, Zaihui;Pokrovskaia, Natalia;Chowdhury, Sultan;Jia, Qi;Chang, Elaine;Khakh, Kuldip;Kwan, Rainbow;McLaren, David G.;Radomski, Chris C.;Ratkay, Leslie G.;Fu, Jianmin;Dales, Natalie A.;Winther, Michael D.. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Application In Synthesis of Thiazol-2-ylmethanamine This article mentions the following:

Stearoyl-CoA deaturase-1 (SCD1) plays an important role in lipid metabolism Inhibition of SCD1 activity represents a potential novel approach for the treatment of metabolic diseases such as obesity, type 2 diabetes and dyslipidemia, as well as skin diseases, acne and cancer. Herein, we report the synthesis and structure-activity relationships (SAR) of a series of novel triazolone derivatives, culminating in the identification of pyrazolyltriazolone (I), a potent SCD1 inhibitor, which reduced plasma C16:1/C16:0 triglycerides desaturation index (DI) in an acute Lewis rat model in a dose dependent manner, with an ED₅₀ of 4.6 mg/kg. In preliminary safety studies, compound I did not demonstrate adverse effects related to SCD1 inhibition after repeat dosing at 100 mg/kg. Together, these data suggest that sufficient safety margins can be achieved with certain SCD1 inhibitors, thus allowing exploration of clin. utility in metabolic disease settings. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Application In Synthesis of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Application In Synthesis of Thiazol-2-ylmethanamine

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

Infrared and Raman study of monophenylthiazoles. Use of force fields of thiazole and benzene in the theoretical calculation of vibrational frequencies. Application to the determination of the dihedral angles of monophenylthiazoles was written by Conte, M.;Mille, G.;Avignon, T.;Metzger, J.. And the article was included in Analusis in 1976.COA of Formula: C9H7NS This article mentions the following:

The ir and Raman spectra of 2-phenyl-, 4-phenyl-, and 5-phenylthiazole are reported. The vibrational force fields of thiazole and of C6H6 are applied to the phenylthiazoles, and the calculations for the normal modes are in good agreement with the vibrational frequency data and assignments. The dihedral angles are 40° for 2-phenylthiazole and 45° for 4-phenyl- and 5-phenylthiazole. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.COA of Formula: C9H7NS

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