Month: February 2023

Ring transformations of heterocyclic compounds. XVII. 2-(2,4,6-triarylphenyl) substituted dihydro-1H-imidazolium, dihydrothiazolium and thiazolium salts from 2-methyl derivatives by pyrylium and thiopyrylium ring transformations was written by Zimmermann, Thomas. And the article was included in Journal of Heterocyclic Chemistry in 1999.Category: thiazole This article mentions the following:

Some new 2-(2,4,6-triarylphenyl)-4,5-dihydro-1H-imidazolium perchlorates, -4,5-dihydrothiazolium perchlorates and -thiazolium perchlorates were obtained from their 2-Me analogs by a 2,6-[C₅+C] ring transformation of 2,4,6-triarylpyrylium and -thiopyrylium salts in ethanol in the presence of an appropriate base. Spectroscopic data of the transformation products and structural influences on their formation via anhydrobases of the triarylpyrylium and -thiopyrylium salts are discussed. In the experiment, the researchers used many compounds, for example, 2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1Category: thiazole).

2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1) 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.Category: thiazole

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

Halogen-substituted thiazole derivatives as corrosion inhibitors for mild steel in 0.5 M sulfuric acid at high temperature was written by Gong, Weinan;Xu, Bin;Yin, Xiaoshuang;Liu, Ying;Chen, Yun;Yang, Wenzhong. And the article was included in Journal of the Taiwan Institute of Chemical Engineers in 2019.Reference of 2103-99-3 This article mentions the following:

The inhibitory effects of three halogen-substituted thiazole derivatives named 2-amino-4-(4-fluorophenyl)-thiazole (FPT), 2-amino-4-(4-chlorophenyl)-thiazole (CPT) and 2-amino-(4-bromophenyl)-thiazole (BPT) on mild steel corrosion were investigated in 0.5 M H₂SO₄ from 30掳C to 60掳C. Electrochem. measurements demonstrated that these thiazoles can effectively inhibit the corrosion of mild steel in 0.5 M H₂SO₄ solution at 30掳C. With the increase of temperature, the inhibition efficiency (畏) of FPT at 60掳C reduced to 22.62% while those of CPT and BPT under the same temperature were nearly unchanged, which were as high as 95.16% and 95.45%, resp. The adsorptions of three thiazoles on the surface of mild steel were all found to adhere to Langmuir adsorption isotherm at 30掳C while only CPT and BPT obeyed at 60掳C. Quantum calculations results indicated that CPT and BPT had the better adsorption ability on mild steel than FPT. Mol. dynamic stimulations were taken out to investigate the adsorption configurations of three thiazoles on the surface of Fe (0 0 1) at 30掳C and 60掳C, and the results implied that the binding energy of protonated BPT and CPT were nearly unchanged at studied temperatures while that of protonated FPT apparently became lower at 60掳C. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Reference of 2103-99-3).

4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Reference of 2103-99-3

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

Unexpected Intermolecular Pd-Catalyzed Cross-Coupling Reaction Employing Heteroaromatic Carboxylic Acids as Coupling Partners was written by Forgione, Pat;Brochu, Marie-Christine;St-Onge, Miguel;Thesen, Kris H.;Bailey, Murray D.;Bilodeau, Francois. And the article was included in Journal of the American Chemical Society in 2006.Name: 4-Methylthiazole-5-carboxylic acid This article mentions the following:

A palladium catalyzed decarboxylative cross-coupling reaction of five-membered heteroaromatic carboxylic acids with aryl bromides for preparing aryl-substituted heteroaromatics has been disclosed. The coupling on the carbon connecting carboxyl group is an attractive complement to the existing C-H functionalization method. In the experiment, the researchers used many compounds, for example, 4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0Name: 4-Methylthiazole-5-carboxylic acid).

4-Methylthiazole-5-carboxylic acid (cas: 20485-41-0) 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.Name: 4-Methylthiazole-5-carboxylic acid

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

Synthesis of gem-Difluorocyclopropa(e)nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF₂Br was written by Li, Lingchun;Wang, Fei;Ni, Chuanfa;Hu, Jinbo. And the article was included in Angewandte Chemie, International Edition in 2013.Product Details of 943-08-8 This article mentions the following:

The authors report the use of TMSCF₂Br as a general difluorocarbene source for the difluoromethylation of alkenes/alkynes initiated by a bromide salt as well as the difluoromethylation of O-, S-, N-, and P-nucleophiles promoted by alk. bases. E.g., in presence of TBAB in PhMe, difluoromethylation of PhC顚咰H with TMSCF₂Br gave 94% difluorocyclopropene (I). E.g., in presence of TMSCF₂Br in CH₂Cl₂ containing 20% aqueous KOH, difluoromethylation of 4-PhC₆H₄OH gave 85% 4-PhC₆H₄OCHF₂. The hydroxyl-ion-promoted fragmentation of TMSCF₂Br at a lower temperature (0 掳C) facilitates the difluoromethylation of (thio)phenols with broad functional group tolerance. The mild reaction conditions of this reaction are also applicable for the difluoromethylation of (thio)alcs., sulfinates, heterocyclic amines, and even hydrophosphine oxides. In the experiment, the researchers used many compounds, for example, 2-((Difluoromethyl)thio)benzo[d]thiazole (cas: 943-08-8Product Details of 943-08-8).

2-((Difluoromethyl)thio)benzo[d]thiazole (cas: 943-08-8) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Product Details of 943-08-8

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

Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates was written by Olawode, Emmanuel O.;Tandlich, Roman;Prinsloo, Earl;Isaacs, Michelle;Hoppe, Heinrich;Seldon, Ronnett;Warner, Digby F.;Steenkamp, Vanessa;Kaye, Perry T.. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2018.Reference of 2103-99-3 This article mentions the following:

A three-step synthesis, involving condensation of bromomethyl aryl ketones with urea to afford 2- aminothiazoles, their chloroacetylation and subsequent solvent-free Arbuzov phosphonation has afforded a series of novel di-Et [N-(thiazol-2-yl)carbamoyl]methylphosphonates 3a–3f in good overall yields; the 4- carboxythiazole analog 3g was obtained by selective hydrolysis of the corresponding Et ester 3f. The phosphonate esters exhibited significant anti-cancer activity (nM – low 渭M IC50 values) against SH-SY5Y cells and, in one case, 7.6渭M MIC90 anti-TB activity against the virulent M. tuberculosis H37Rv strain; the chloroacetamido precursors all exhibited some antimalarial (PfLDH) activity, three with IC50 values in the range 1.0 – 8.9渭螠. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Reference of 2103-99-3).

4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Reference of 2103-99-3

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

Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents was written by Wang, Min;Gao, Mingzhang;Mock, Bruce H.;Miller, Kathy D.;Sledge, George W.;Hutchins, Gary D.;Zheng, Qi-Huang. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Recommanded Product: 2-Amino-5-fluorobenzothiazole This article mentions the following:

Fluorinated 2-arylbenzothiazoles are new potential antitumor drugs, which show potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Carbon-11 labeled fluorinated 2-arylbenzothiazoles may serve as novel probes for positron emission tomog. (PET) to image tyrosine kinase in cancers. The preparation of 4-fluorinated 2-arylbenzothiazoles 4-fluoro-2-(3-benzloxy-4-methoxyphenyl)benzothiazole (6a) and 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (6b) was achieved by a modification of Jacobson thioanilide radical cyclization chem. Hydrogenolytic cleavage of the benzyl ether group of compound 6a using H₂/Pd-C provided the precursor 4-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole (7) for radiolabeling. Synthesis of radiolabeling precursors and the reference standards 5- and 6-fluorinated arylbenzothiazoles (11c-n) was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. The target radiotracers carbon-11 labeled 4-, 5-, and 6-fluorinated arylbenzothiazoles were prepared by O-[¹¹C]methylation of the phenolic hydroxyl precursors with [¹¹C]methyl triflate and isolated by solid-phase extraction (SPE) purification in 30-55% radiochem. yields. In the experiment, the researchers used many compounds, for example, 2-Amino-5-fluorobenzothiazole (cas: 20358-07-0Recommanded Product: 2-Amino-5-fluorobenzothiazole).

2-Amino-5-fluorobenzothiazole (cas: 20358-07-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Recommanded Product: 2-Amino-5-fluorobenzothiazole

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

Antagonist- and inverse agonist-driven interactions of the vitamin D receptor and the constitutive androstane receptor with corepressor protein was written by Lempiainen, Harri;Molnar, Ferdinand;Gonzalez, Manuel Macias;Perakyla, Mikael;Carlberg, Carsten. And the article was included in Molecular Endocrinology in 2005.Electric Literature of C19H12Cl3N3OS This article mentions the following:

Ligand-dependent signal transduction by nuclear receptors (NRs) includes dynamic exchanges of coactivator (CoA) and corepressor (CoR) proteins. Here the authors focused on the structural determinants of the antagonist- and inverse agonist-enhanced interaction of the endocrine NR vitamin D receptor (VDR) and the adopted orphan NR constitutive androstane receptor (CAR) from two species with the CoR NR corepressor. The authors found that the pure VDR antagonist ZK168281 and the human CAR inverse agonist clotrimazole are both effective inhibitors of the CoA interaction of their resp. receptors, whereas ZK168281 resembled more the mouse CAR inverse agonist androstanol in its ability to recruit CoR proteins. Mol. dynamics simulations resulted in comparable models for the CoR receptor interaction domain peptide bound to VDR/antagonist or CAR/inverse agonist complexes. A salt bridge between the CoR and a conserved lysine in helix 4 of the NR is central to this interaction, but also helix 12 was stabilized by direct contacts with residues of the CoR. Fixation of helix 12 in the antagonistic/inverse agonistic conformation prevents an energetically unfavorable free floatation of the C terminus. The comparable mol. mechanisms that explain the similar functional profile of antagonist and inverse agonists are likely to be extended from VDR and CAR to other members of the NR superfamily and may lead to the design of even more effective ligands. In the experiment, the researchers used many compounds, for example, 6-(4-Chlorophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde O-(3,4-dichlorobenzyl) oxime (cas: 338404-52-7Electric Literature of C19H12Cl3N3OS).

6-(4-Chlorophenyl)imidazo[2,1-b]thiazole-5-carbaldehyde O-(3,4-dichlorobenzyl) oxime (cas: 338404-52-7) 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. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Electric Literature of C19H12Cl3N3OS

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

Condensation of aromatic amines with nitrosobenzene in basic medium. II. Heteroaromatic amines was written by Pentimalli, Luciano;Milani, Giovanni. And the article was included in Annali di Chimica (Rome, Italy) in 1989.Category: thiazole This article mentions the following:

Aminobenzothiazoles, -naphthothiazoles and -1,2,4-thiadiazoles condense, in alk. medium, with nitrosobenzene as well as its 4-chloro derivative to give the corresponding azo compounds Aminothiazoles and -1,3,4-thiadiazoles did not give condensation products. 4-Nitro- and 4-dimethylaminonitrosobenzene gave the corresponding azoxybenzene as main reaction product. In the experiment, the researchers used many compounds, for example, Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4Category: thiazole).

Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Category: thiazole

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

Correlation between the inhibiting action of 2-aminothiazoles and their electron structure was written by Mal’tseva, V. P.;Momsenko, A. P.. And the article was included in Zashchita Metallov in 1979.Application In Synthesis of Naphtho[1,2-d]thiazol-2-amine This article mentions the following:

Quantum chem. calculations were made for electron structure of 2-aminobenzothiazole [136-95-8] (I), 2-aminonaphtho-1,2,4,5-thiazole [40172-65-4] (II), and 2-amino-4,5,6,7-tetrahydrobenzothiazole [2933-29-1] (III). Their corrosion inhibition and polarization voltage were determined in 1N HCl and 1N H₂SO₄ for steel St2 [12742-82-4] and St 3 [39296-41-8]. Corrosion rate reductions were 85-87, 90.4-93.5, and 96-99.5% for I, II, and III, resp. The mols. showed effective charge separation on N and S. In the experiment, the researchers used many compounds, for example, Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4Application In Synthesis of Naphtho[1,2-d]thiazol-2-amine).

Naphtho[1,2-d]thiazol-2-amine (cas: 40172-65-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Application In Synthesis of Naphtho[1,2-d]thiazol-2-amine

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

Nitrogen bridgehead compounds. Part 67. Preparation of novel polycyclic quaternary salts was written by Bitter, Istvan;Pete, Bela;Agai, Bela;Toke, Laszlo;Toth, Gabor;Hermecz, Istvan;Simon, Kalman;Meszaros, Zoltan;Parkanyi, Laszlo. And the article was included in Heterocycles in 1987.Computed Properties of C4H7NS This article mentions the following:

The cycloaddition reaction of (aminochloromethylene)pyridopyrimidines I (R¹ = CO₂Et, cyano) with 3,4-dihydroisoquinolines gave ioquinodiazaazoniaphenalene salts II (R² = H, Me; R³ = H, OMe; X = Cl, ClO₄). Similarly fused compounds were obtained from 2-thiazoline and 2-oxazoline derivatives, benzothiazole, and a benzoxazole derivative The crystal and mol. structure of II (R¹ = cyano, R² = R³ = H, X = Cl) were obtained. In the experiment, the researchers used many compounds, for example, 2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1Computed Properties of C4H7NS).

2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1) 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.Computed Properties of C4H7NS

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