Tag: 200-300

A practical synthesis of 2-aminobenzothiazoles via copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in ionic liquids was written by Chen, Ling;Huang, Bin;Nie, Quan;Cai, Mingzhong. And the article was included in Applied Organometallic Chemistry in 2016.Reference of 1843-21-6 This article mentions the following:

A copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates was achieved in hydrophobic [bmim][PF₆] ionic liquid under mild conditions, generating a variety of 2-aminobenzothiazoles in good to excellent yields. The tandem reaction that was carried out in [bmim][PF₆] has some obvious advantages such as accelerated reaction rate and increased yield as compared with the reaction run in volatile solvents such as toluene. Furthermore, the CuI/1,10-phenanthroline catalytic system can be reused up to eight times without loss of activity and efficiency. 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. 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. 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.Reference of 1843-21-6

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

The reaction of benzothiazolyl substituted α-phosphorylmethyl sulfoxides with several amines was written by Morita, Hiroyuki;Tashiro, Shintaro;Takeda, Masahiro;Yamada, Nobuhiko;Sheikh, Chanmiya Md.;Kawaguchi, Hiroyuki. And the article was included in Tetrahedron in 2008.COA of Formula: C13H10N2S This article mentions the following:

The reactivities of α-phosphorylmethyl benzothiazolyl sulfoxides in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, morpholine, and pyrrolidine was examined Thermolyses of the derivatives in the presence of 2,3-dimethyl-1,3-butadiene afforded 2-phosphoryl substituted 4,5-dimethyl-3,6-dihydro-2H-thiopyran S-oxide. In the reaction with amines, the complex product mixture, which contains α-phosphorylmethyl benzothiazolyl sulfides, α-phosphorylmethyl disulfides, and 2-amino substituted benzothiazole was formed besides the target phosphinecarbothioamides. Several mechanistic studies were performed to elucidate the formation mechanism, particularly for deoxygenated products from the starting sulfoxides. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.COA of Formula: C13H10N2S

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

C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates was written by Zi, You;Schoemberg, Fritz;Wagner, Konrad;Vilotijevic, Ivan. And the article was included in Organic Letters in 2020.Application of 1843-21-6 This article mentions the following:

Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- and N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

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.Application of 1843-21-6

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

The rates of reaction of α-halo ketones with thiosemicarbazides was written by Okamiya, Jiro. And the article was included in Nippon Kagaku Zasshi in 1962.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

The rates of reaction of phenacyl bromides with thiosemicarbazides were determined by conductivity measurement in EtOH. The reaction is second order up to 85% completion; the rate constant is obtained. The activation energies are 10.511.3 kcal./mole for the reaction of H₂NCSNHNHPh (I) and 8.5-9.3 kcal./mole for H₂NCSNHNH₂ (II). The activation energy for the reaction between PhC(:NOH)CH₂Br and NH₂CSNH₂ (III) or II is obtained as 10.2 or 6.6 kcal./mole. Thus, the reaction rate is shown as III > II > I and the reaction of oximes is much slower than that of the parent α-halo ketone itself. Hammett’s rule is applicable to the reaction and p is obtained as 0.63 and 0.74 for I and II, resp. The reaction products, 2-amino-5-(p-aminophenyl)thiazoles were prepared Bromomethyl ketone (0.003 mole), 0.003 mole I, and 20 cc. EtOH were heated 2 hrs., heated 30 min. after addition of 1 cc. HCl, 50 cc. H₂O added, and the mixture filtered after boiling and basified with NH₃ to give 55-90% yield. Methyl ketone, iodine, and I were heated 8 hrs. and treated similarly to give 40-70% yield. Thus, the following 4-substituted 2-amino-5(p-aminophenyl)thiazoles (IV) are obtained (R and m. p. given): H, 204°; Ph, 200-1°; p-MeC₆H₄, 190°; o-MeC₆H₄,210°; p-MeOC₆H₄, 237°; p-ClC₆H₄, 224°; p-BrC₆H₄, 247°; m-BrC₆H₄, 213-14°; m-IC₆H₄, 261°; m-IC₆H₄, 195°; m-O₂NC₆H₄, 252°; m-O₂NC₆H₄, 231°; o-O₂NC₆H₄, 241°; p-H₂NC₆H₄, 111° and 223° (double m.p.); p-PhC₆H₄, 237°; α-C₁₀₀H₇, 155°. KOH (5 g.) in 5 cc. H₂O was saturated with H₂S and 5 g. PhCOCHBrPh in 10 cc. EtOH added to give 2.5 g. PhCOCH₂Ph (V) after 2 hrs. heating. PhCOCHClPh (1.1 g.) in EtOH and III EtOH were mixed and heated 2 hrs. with 3.5 cc. 3N NaOH after standing 3 hrs. to give 0.1 g. V and 0.8 g. 2-amino-4,5diphenylthiazole, m. 188°. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 4,5-Diphenylthiazol-2-amine

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

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

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

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

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

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