Month: February 2023

An environmentally benign synthesis of Tetrabutylphosphonium tribromide (TBPTB) – a versatile and efficient phase transfer reagent for organic transformations was written by Kuotsu, Visekhonuo;Nakro, Vevosa;Yanger, Imkong;Lotha, Tsenbeni N.;Tzudir, Ketiyala;Sinha, Upasana Bora;Jamir, Latonglila. And the article was included in Green Chemistry Letters and Reviews in 2021.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Tetrabutylphosphonium tribromide (TBPTB), a mild and versatile reagent, has been synthesized following an environmentally benign protocol. The new reagent possesses inherent phase transfer properties which facilitates organic reactions in aqueous medium. Thermal stability of the reagent which enables organic reactions under microwave irradiation and recyclability of the spent reagent are special attributes of the new reagent. These properties collectively provide an opportunity for facile, practical, and eco-friendly synthesis of a wide range of pharmaceutically significant and specialty organic compounds such as bromo-organics, isothiocyanates, cyanamides and 2-aminobenzothiazoles in excellent yields on-water under microwave irradiation In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine

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

Postsynthetic modification of IRMOF-3 with a copper (imino)pyridine complex as heterogeneous catalyst for the synthesis of 2a[̂n.128]aminobenzothiazoles was written by Liu, Jie;Zhang, Xiaobin;Yang, Jin;Wang, Lei. And the article was included in Applied Organometallic Chemistry in 2014.Category: thiazole This article mentions the following:

A copper imine-pyridine complex was immobilized on to a metal-organic framework (MOF) by a h postsynthetic modification of IRMOF-3. The modified MOFs were fully demonstrated by using a variety of methods and the structural integrity of the modified MOFs was confirmed by powder X-ray diffraction (XRD). Furthermore, it was shown that the modified IRMOF-3 can act as an efficient solid catalyst for the synthesis of 2-aminobenzothiazoles via the reaction of 2-iodoanilines with isothiocyanates in a heterogeneous manner. Moreover, the catalyst could be easily separated from the reaction mixture and reused for six consecutive cycles without significant degradation in catalytic activity. The synthesis of the target compound (catalyst) was achieved by a reaction of (amino)benzenedicarboxylic acid and zinc nitrate reaction product [i.e, isoreticular metal-organic framework (IRMOF-3)] with 2-pyridinecarboxaldehyde, thus providing an isoreticular metal-organic framework (IRMOF-3) supported N-[(pyridinyl)methylene]benzenamine (Schiff base imine) which underwent complexation with copper iodide (CuI). The product was copper-N-[(pyridinyl)methylene]benzenamine (Schiff base imine) complex supported on isoreticular metal-organic framework (IRMOF-3). Starting materials included (isothiocyanato)benzene (isothiocyanate), 2-iodobenzenamine derivatives (aryl iodides, iodo aniline derivatives), 1-isothiocyanato-3,5-bis(trifluoromethyl)benzene, etc. The title compounds thus formed included N-phenyl-2-benzothiazolamine derivatives and related substances, such as 6-fluoro-N-(4-methylphenyl)-2-benzothiazolamine, N-(4-chlorophenyl)-6-(trifluoromethyl)-2-benzothiazolamine. Copyright 2014 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Microwave assisted one pot synthesis of 2-alkyl amino benzimidazoles, 2-alkyl amino benzoxazoles and 2-alkyl amino benzthiazoles by using various carbodiimides was written by Rapolu, Thirupathi;Naveen, Polkam;Pavan Kumar, K. V. P.;Reddy Leleti, Krishnakanth;korapolu, Raghubabu. And the article was included in Results in Chemistry in 2022.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A library of bioisosteres namely 2-amino substituted benzimidazole, 2-amino substituted benzoxazole, 2-amino substituted benzthiazole derivatives were synthesized by an efficient ligand free, zinc catalyzed one-pot cascade microwave irradiation technique. The procedure started with coupling of various carbodiimides with appropriately substituted o-phenylendiamine, o-aminophenol and o-aminothiols to give the corresponding derivatives in excellent yields. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Quality Control of N-Phenylbenzo[d]thiazol-2-amine

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

Discovery and evolution of aloperine derivatives as a new family of HCV inhibitors with novel mechanism was written by Zhang, Xin;Lv, Xiao-Qin;Tang, Sheng;Mei, Lin;Li, Ying-Hong;Zhang, Jing-Pu;Jiang, Jian-Dong;Peng, Zong-Gen;Song, Dan-Qing. And the article was included in European Journal of Medicinal Chemistry in 2018.SDS of cas: 69812-29-9 This article mentions the following:

Aloperine (I), a Chinese natural product with a unique endocyclic scaffold, was first identified to be a potent hepatitis C virus (HCV) inhibitor in our laboratory Thirty-four new aloperine derivatives were designed, synthesized and evaluated for their anti-HCV activities taking I as the lead. Among them, compound II exhibited the potential potency with EC₅₀ values in a micromolar range against both wild-type and direct-acting antiviral agents (DAAs)-resistant variants, and synergistically inhibited HCV replication with approved DAAs. Furthermore, it also owned a good oral pharmacokinetic and safety profile, suggesting a highly druglike nature. The primary mechanism showed that II might target host components, distinctly different from the DAAs currently used in clinic. Therefore, we consider aloperine derivatives to be a novel class of anti-HCV agents, and compound II has been selected as a promising antiviral candidate for further investigation. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9SDS of cas: 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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 pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.SDS of cas: 69812-29-9

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

The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D₃ Receptor (D₃R) Selective Agonists was written by Battiti, Francisco O.;Cemaj, Sophie L.;Guerrero, Adrian M.;Shaik, Anver Basha;Lam, Jenny;Rais, Rana;Slusher, Barbara S.;Deschamps, Jeffery R.;Imler, Greg H.;Newman, Amy Hauck;Bonifazi, Alessandro. And the article was included in Journal of Medicinal Chemistry in 2019.Recommanded Product: 68867-17-4 This article mentions the following:

Because of the large degree of homol. among dopamine D₂-like receptors, discovering ligands capable of discriminating between the D₂, D₃, and D₄ receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chem. modification of the D₃ preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D₃R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D₃R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D₃R binding selectivities than the reference compounds Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Recommanded Product: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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: 68867-17-4

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

Novel diphenylthiazole derivatives with multi-target mechanism: Synthesis, docking study, anticancer and anti-inflammatory activities was written by Abdelazeem, Ahmed H.;El-Saadi, Mohammed T.;Said, Eman G.;Youssif, Bahaa G. M.;Omar, Hany A.;El-Moghazy, Samir M.. And the article was included in Bioorganic Chemistry in 2017.Product Details of 6318-74-7 This article mentions the following:

Over the last few decades, a growing body of studies addressed the anticancer activity of NSAIDs, particularly selective COX-2 inhibitors. However, their exact mol. mechanism is still unclear and is not fully investigated. In this regard, a novel series of compounds bearing a COXs privilege scaffold, di-Ph thiazole, was synthesized and evaluated for their anticancer activity against a panel of cancer cell lines. The most active compounds 10b, 14a,b, 16a, 17a,b and 18b were evaluated in vitro for COX-1/COX-2 inhibitory activity. These compounds were suggested to exert their anticancer activity through a multi-target mechanism based on their structural features. Thus, compounds 10b and 17b with the least IC₅₀ values in MTT assay were tested against three known anticancer targets; EGFR, BRAF and tubulin. Compounds 10b and 17b showed remarkable activity against EGFR with IC₅₀ values of 0.4 and 0.2 μM, resp. and good activity against BRAF with IC₅₀ values of 1.3 and 1.7 μM, resp. In contrast, they showed weak activity in tubulin polymerization assay. The in vivo anti-inflammatory potential was assessed and interestingly, compound 17b was the most potent compound Together, this study offers some important insights into the correlation between COXs inhibition and cancer treatment. Addnl., the results demonstrated the promising activity of these compounds with a multi-target mechanism as good candidates for further development into potential anticancer agents. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Product Details of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Product Details of 6318-74-7

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

A Cu₂O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water was written by Zhang, Jinli;Chen, Ling;Dong, Yibo;Yang, Jinchen;Wu, Yangjie. And the article was included in Organic & Biomolecular Chemistry in 2020.Formula: C13H10N2S This article mentions the following:

An efficient approach to synthesize heteroaromatic 2-amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to synthesize heteroaromatic 2-amines in moderate to excellent yields. A plausible mechanism was proposed and the role of TBAB and Cu₂O in the present strategy was suggested with the help of ESI mass spectrometry. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Formula: C13H10N2S

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

Synthesis and fungicidal activity of N,S-substituted α-thio-β-aminocrotonanilides was written by Pierce, James B.;Fanning, Robert J.;Davis, Robert Allan. And the article was included in Canadian Journal of Chemistry in 1975.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A number of N,S-substituted α-thio-β-aminocrotonanilides have been synthesized. Their fungicidal activity on a number of organisms has been studied and in general it has been found that it is inferior to that of the 1,4-oxathiins to which these compounds bear some structural similarities. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine

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

Synthesis of 2-mercaptobenzothiazole using nitrobenzene and H₂S as starting materials was written by Li, Jinghua;Li, Zhenqiu;Yu, Guang;Song, Yuye. And the article was included in Qingdao Keji Daxue Xuebao, Ziran Kexueban in 2009.Reference of 1843-21-6 This article mentions the following:

H₂S which was the byproduct from 2-mercaptobenzothiazole synthesis process reacted with nitrobenzene to prepare aniline and the obtained aniline was directly used to synthesize 2-mercaptobenzothiazole. The sulfur obtained from reduction process was used as material for synthesizing 2-mercaptobenzothiazole. That is to say the byproducts H₂S and sulfur could be utilized circularly. Under the conditions of 80-100°C, certain pressure and 3-4 h, the yield of aniline could reach 6.619%. The feasibility of experiment was done by directly adding sulfur dissolved in carbon disulfide into the reduction mixture to prepare 2- mercaptobenzothiazole. A new clean synthesis method of 2-mercaptobenzothiazole with lower cost is explored. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Reference of 1843-21-6

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