Day: December 30, 2022

Pyrolyses of 2-aminobenzazoles was written by Martineau, Andre;DeJongh, Don C.. And the article was included in Journal of Analytical and Applied Pyrolysis in 1983.Category: thiazole This article mentions the following:

The pyrolysis and mass spectral fragmentation of I (R = Ph, H; X = O, NH, S) follow similar paths and mechanisms. The replacement of H in I (R = H) by Ph allowed the observation of reaction intermediates, in both the pyrolysis and the mass spectra, which were too unstable for direct observation with I (R = H); the Ph group behaved as an internal trapping group. The M⁺ and (M – H)⁺ peaks are the most intense mass spectral peaks for I. 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. 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Nucleophilic reactivity of 2-chlorobenzothiazole was written by Todesco, Paolo Edgardo;Vivarelli, Piero. And the article was included in Gazzetta Chimica Italiana in 1962.Category: thiazole This article mentions the following:

The reaction of MeONa with 5- or 6-substituted derivatives of 2-chlorobenzothiazole has been studied. 2-Chlorobenzothiazole (I), b₂₁ 133-4°, was prepared according to Moon (CA 43, 6670c). The 6-nitro derivative (II) of I, pale yellow needles, m. 191-2°, was prepared by nitrating I with KNO₃ and H₂SO₄ (U.S. 2,659,730, CA 49, 2519a; Katz, CA 46, 3044b). The 5-nitro derivative (III) of I, m. 112°, was prepared by adding an excess of SO₂Cl₂, in the cold, to 0.003 mole of 2-mercapto-5-nitrobenzothiazole, crude m. 223-5°, prepared in turn in 60% yield, by adding a KSH solution (0.01 mole KOH in little water and 30 ml. alc., saturated with H₂S) to a boiling alc. solution of 2-bromo-5-nitroaniline, cooling, adding 0.3 ml. CS₂, stirring 4 hrs. at 80°, steam distilling, cooling, making ammoniacal, filtering off S, and precipitating the product by making acid with HCl. The 4-nitro derivative (IV) of I, yellow needles, m. 169-70°, was prepared by diazotizing 2-amino-4-nitrobenzothiazole (Erlenmeyer and Ueberwasser, CA 34, 2844⁶), m. 254°, and decomposing the diazonium salt with cold Cu₂Cl₂-HCl. The 6-methyl derivative (V) of I, m. 49-50°, resulted from 2-amino-6-methylbenzothiazole, m. 135-6°, according to Metzger and Plank (CA 50, 15512a). The 5-methyl derivative (VI) of I, m. 41-2° (cold pentane) was made by treating 2-mercapto-4-methylbenzothiazole with SO₂Cl₂, the intermediate being prepd, according to Teppema and Sebrell (CA 21, 2688). The 6-chloro derivative (VII) of I, m. 98-9°, was prepared by diazotizing 2-amino-6-chlorobenzothiazole, m. 200°, in a mixture of HCO₂H, AcOH, and HCl, and decomposing the diazo salt with Cu₂Cl₂-HCl (Stuckwisch, CA 44, 2514a). The intermediate was obtained according to Kaufmann and Kuchler (CA 28, 5066⁶). The 5-chloro derivative (VIII) of I, m. 70-1°, was prepared by treating 2-mercapto-5-chlorobenzothiazole, m. 196-7°, with SO₂Cl₂. The 6-methoxy derivative (IX) of I, m. 53-4°, was prepared according to Stuckwisch (loc. cit.). For the reaction with Me-ONa, MeOH solutions of the reagents, previously brought to reaction temperature, were mixed and kept at const, temperature, taking samples at intervals and pouring them into an excess of aqueous HNO₃, followed by AgNO₃, and determining Cl^– by the Volhard method. The resulting data were plotted and used to calculate the rate constant and energy of activation of the reactions. The second-order rate const, k (10³ sec.^-1 mole^–1) for 0°, 13°, 25°, 35°, and 45°, followed by the activation energy E (kcal. mole^-1) for the various derivatives of I: I, -, -, 0.55, 1.43, 3.39, 16.9; IV, -, 42.8, 132.0, 335.0, -, 16.3; III, 8.09, -, 87.8, 205.0, -, 15.4; VIII,-, 2.53, 6.37, 15.20, -, 15.8; VI, -, 0.116, 0.374, 1.05, -, 17.8; II, -, 97.0, 280.0, 647.0, -, 14.2; VII, -, 1.01, 3.25, 7.79, -, 16.0; V, -, 0.057, 0.197, 0.578, -, 18.3; and IX, -, 0.0244, 0.0893, 0.255, -, 18.7. Electron-attracting substituents (Cl, NO₂) speed up the reaction, while electron-donor substituents (Me, MeO) slow it down. The log k of the reaction gave a straight line function of Hammett’s σ (of. Jaffe, Chem. Rev. 53, 191(1953)), except in the case of II. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Category: thiazole).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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.Category: thiazole

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

Facile synthesis of the new tripodal tetraamine ligand tris(thiazolylmethyl) amine, and full characterization of two ferrous complexes was written by Thibon, Aurore;Karmazin-Brelot, Lydia;Mandon, Dominique. And the article was included in Dalton Transactions in 2013.Quality Control of Thiazol-2-ylmethanamine This article mentions the following:

The authors report the facile synthesis of the new tris(thiazolylmethyl)amine, TTA ligand (3) and the full characterization in solution and in the solid state of two ferrous complexes, [(TTA)FeCl₂] (1) and [(TTA)Fe(OTf)₂] (2). TTA, the first example of a simple tris(thiazolemethyl)amine chelate – the second one only within this class of tripods – exerts a weak ligand field and the tertiary amine is weakly bound to the metal center. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Quality Control of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Quality Control of Thiazol-2-ylmethanamine

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

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan was written by Lv, Fengping;Li, Zhi-fang;Hu, Wenhao;Wu, Xiaohua. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Category: thiazole This article mentions the following:

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biol. processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chem. stimuli, the authors developed a cell-based high-throughput screening (HTS) platform for searching chem. enhancers of FOG of α-DG from a large chem. library with 364,168 compounds Sequential validation of the hits from a primary screening campaign and chem. works led to identification of a cluster of compounds that pos. modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Category: thiazole).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Category: thiazole

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

Design and Synthesis of Imidazo[2,1-b]thiazole-Chalcone Conjugates: Microtubule-Destabilizing Agents was written by Kamal, Ahmed;Balakrishna, Moku;Nayak, V. Lakshma;Shaik, Thokhir Basha;Faazil, Shaikh;Nimbarte, Vijaykumar D.. And the article was included in ChemMedChem in 2014.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

A series of chalcone conjugates featuring the imidazo[2,1-b]thiazole scaffold was designed, synthesized, and evaluated for their cytotoxic activity against five human cancer cell lines (MCF-7, A549, HeLa, DU-145 and HT-29). These new hybrid mols. have shown promising cytotoxic activity with IC₅₀ values ranging from 0.64 to 30.9 μΜ. Among them, (E)-3-(6-(4-fluorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)-1-(pyridin-2-yl)prop-2-en-1-one (11 x) showed potent antiproliferative activity with IC₅₀ values ranging from 0.64 to 1.44 μΜ in all tested cell lines. To investigate the mechanism of action, the detailed biol. aspects of this promising conjugate (11 x) were carried out on the A549 lung cancer cell line. The tubulin polymerization assay and immunofluoresence anal. results suggest that this conjugate effectively inhibits microtubule assembly in A549 cells. Flow cytometric anal. revealed that this conjugate induces cell-cycle arrest in the G2/M phase and leads to apoptotic cell death. This was further confirmed by Hoechst staining, activation of caspase-3, DNA fragmentation anal., and Annexin V-FITC assay. Moreover, mol. docking studies indicated that this conjugate (11 x) interacts and binds efficiently with the tubulin protein. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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 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 4,5-Diphenylthiazol-2-amine

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

Computational studies of effective asymmetric alkylation utilizing a chiral Schiff base derived from 2-hydroxy-3-pinanone. Part 1 was written by Matsumoto, Takatoshi;Shiori, Takayuki;Osawa, Eiji. And the article was included in Tetrahedron in 1996.Name: Thiazol-2-ylmethanamine This article mentions the following:

The calculation by the semi-empirical MO method concerning the mechanism of the effective asym. alkylation utilizing a chiral Schiff base derived from 2-hydroxy-3-pinanone (I) has revealed that the factor which controls the stereoselectivity is mainly the influence of the lithium and THF ligands. The results has demonstrated the proposed hypothesis which is based on many experiments In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Name: Thiazol-2-ylmethanamine).

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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Name: Thiazol-2-ylmethanamine

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

Design, Synthesis, and Anti-Inflammatory Evaluation of Novel Diphenylthiazole-Thiazolidinone Hybrids was written by Abdelazeem, Ahmed H.;Salama, Samir A.;Maghrabi, Ibrahim A.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2015.Name: 4,5-Diphenylthiazol-2-amine This article mentions the following:

A series of diphenylthiazole-thiazolidinone hybrids was synthesized and evaluated in vitro and in vivo as anti-inflammatory/analgesic agents. The inhibition of cyclooxygenase (COX) enzymes was suggested as a mol. mechanism for the hybrids to exert their anti-inflammatory action. Of these compounds, 2-((4,5-diphenylthiazol-2-yl)imino)-5-(pyridin-3yl-methylene)thiazolidin-4-one (1), 2-((4,5-diphenylthiazol-2-yl)imino)-5-(naphthalen-1-yl-methylene)thiazolidin-4-one (2), and 2-((4,5-diphenylthiazol-2-yl)imino)-5-(3-nitrobenzylidene)thiazolidin-4-one (3) showed the most potent COX inhibitory activity with IC₅₀ values between 2.03 and 12.27 μM, but with different selectivity profiles. All compounds were further evaluated in vivo for their anti-inflammatory/analgesic activities using three animal models. Interestingly, the results of the COX assay were in agreement with those of in vivo assays where the most potent COX inhibitors 1, 2, and 3 exhibited the highest anti-inflammatory/analgesic activities compared to diclofenac. On the contrary, 2-((4,5-diphenylthiazol-2-yl)imino)thiazolidin-4-one and 2-((4,5-diphenylthiazol-2-yl)imino)-5-(thiophen-2-yl-methylene)thiazolidin-4-one were the least potent ligands in vitro and in vivo as well. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Name: 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Name: 4,5-Diphenylthiazol-2-amine

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

Response surface optimization of Smyrnium cordifolium Boiss (SCB) oil extraction via supercritical carbon dioxide was written by Sodeifian, Gh.;Azizi, J.;Ghoreishi, S. M.. And the article was included in Journal of Supercritical Fluids in 2014.Recommanded Product: 5-Phenylthiazole This article mentions the following:

In this study, the essential oil of aerial parts of a species of a plant called Smyrnium cordifolium Boiss (SCB) was extracted by supercritical CO₂. The essence was analyzed by the method of GC/MS. Design of experiments was carried out with response surface methodol. by Minitab 16 software to optimize four operating variables of supercritical carbon dioxide (SC-CO₂) extraction (pressure, temperature, CO₂ flow rate and extraction dynamic time). This is the first report announcing optimization of the operation of supercritical extraction of SCB in laboratorial conditions. Optimizing process was done to achieve maximum yield extraction Independent variables were dynamic time (t_d), pressure (P), temperature (T) and flow rate of SC-CO₂ (Q) in the range of 30-150 min, 10-30 MPa, 40-60 °C and 0.5-1.7 mL/min, resp. The exptl. optimal recovery of essential oil (0.8431, weight/weight %) was obtained at 13.43 MPa, 40 °C, 150 min (dynamic) and 1.7 mL/min (CO₂ flow rate). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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: 5-Phenylthiazole

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

A convenient synthesis of 2-mercapto- and 2-chlorobenzothiazoles was written by Zhu, Lei;Zhang, Mingbao;Dai, Miao. And the article was included in Journal of Heterocyclic Chemistry in 2005.Quality Control of 5-Nitrobenzothiazole-2-thiol This article mentions the following:

A convenient synthesis of 2-mercapto and 2-chlorobenzothiazoles is described. The key feature of the synthesis is an exclusive ortho-selective nucleophilic aromatic substitution reaction of ortho-haloanilines with potassium/sodium O-Et dithiocarbonate under mild conditions. Subsequent intra-mol. cyclization affords 2-mercaptobenzothiazoles in high yields. The 2-mercaptobenzothiazoles are readily converted to corresponding 2-chlorobenzothiazoles upon treatment with sulfuryl chloride. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Quality Control of 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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.Quality Control of 5-Nitrobenzothiazole-2-thiol

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

A new and efficient synthesis of 2-aminobenzothiazoles derivatives from o-nitroaniline was written by Mirza, Behrooz;Mirzazadeh, Roghieh;Zeeb, Mohsen. And the article was included in Journal of Chemical Research in 2013.Computed Properties of C13H10N2S This article mentions the following:

A novel synthesis of 2-aminobenzothiazoles from a transition-metal-free reaction between aryl isothiocyanates and o-nitroaniline in the presence of K₂CO₃ was reported. The newly developed method is an efficient and cost-effective approach to synthesize 2-aminobenzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

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. 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 C13H10N2S

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