Category: thiazole

Synthesis and molecular docking of new roflumilast analogues as preferential-selective potent PDE-4B inhibitors with improved pharmacokinetic profile was written by Moussa, Bahia A.;El-Zaher, Asmaa A.;El-Ashrey, Mohamed K.;Fouad, Marwa A.. And the article was included in European Journal of Medicinal Chemistry in 2018.Related Products of 6294-52-6 This article mentions the following:

In the present work, a new series of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(benzo[d]thiazolyl)benzamides I [R = 1,3-benzothiazol-2-yl, 1,3-benzothiazol-6-yl, 6-F-1,3-benzothiazol-2-yl, etc.] and N-(thiazol-2-yl)benzamide I [R = thiazol-2-yl] was designed and synthesized via coupling reaction of 3-cyclopropylmethoxy-4-difluoromethoxybenzoic acid with aminobenzothiazoles/2-aminothiazole. These new roflumilast analogs I showed preferential-selective PDE-4B inhibition activity and improved pharmacokinetic properties. The unsubstituted benzo[d]thiazolyl-benzamide derivatives I [R = 1,3-benzothiazol-2-yl, 1,3-benzothiazol-6-yl] showed both good potency and preferential selectivity for PDE-4B and compound I [R = 2-sulfanyl-1,3-benzothiazol-6-yl] revealed six times preferential PDE-4B/4D selectivity with a significant increase of in vitro cAMP and good % inhibition of TNF-α concentration In addition, the in vitro pharmacokinetics of compound I [R = 2-sulfanyl-1,3-benzothiazol-6-yl] showed good metabolic stability with in vitro CL_int (5.67 mL/min/kg) and moderate % plasma protein binding (53.71%). Mol. docking of compound I [R = 2-sulfanyl-1,3-benzothiazol-6-yl] attributed its good activity to its key binding interactions in PDE-4B active site with addnl. hydrogen bonding with amino acids lining the metal pocket. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Related Products of 6294-52-6).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Related Products of 6294-52-6

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

p-Bis(2-chloroethyl)aminophenylalanine (sarcolysine) and its derivatives. VI. Amides of N-acetylsarcolysine and some amines of the thiazole series was written by Berlin, A. Ya.;Bronovitskaya, V. P.. And the article was included in Zhurnal Obshchei Khimii in 1961.Category: thiazole This article mentions the following:

Heating thiazole with 40% HCHO in an autoclave 6 hrs. at 120° gave (after treatment with aqueous K₂CO₃ then 1:1 HCl) 22.5% 2-(hydroxymethyl)thiazole-HCl, m. 126.5-7°, which with SOCl₂ in CHCl₃, finally at reflux 1.5 hrs., gave 77% 2-(chloromethyl)thiazole, b₅ 62° (picrate m. 126.5-7.5°). Crude 5-(hydroxymethyl)thiazole gave HCl salt, m. 83-4°, which with SOCl₂ gave 78.6% 5-(chloromethyl)thiazole, isolated as picrate, m. 103-4°; free base, undistilable oil. The chloromethyl derivatives with o-C₆H₄(CO)₂NK in 2 hrs. at 150-80° gave 2-phthalimidothiazole, m. 117-18°, 4-isomer, m. 157-8°, and 2-methyl-4-phthalimidothiazole, m. 146-6.5°, in 58-63% yield. These refluxed in EtOH with N₂H₄.H₂O gave 2-(aminomethyl)thiazole, b₁₄ 93-5° (HCl salt m. 186-7°), 4-(aminomethyl)thiazole-HCl, m. 212-13°, and 2-methyl-4-(aminomethyl)thiazole, b₂₂ 106-7°, n²⁰_D 1.553. The 5-(chloromethyl)thiazole was very unstable and its reaction with K phthalimide failed to give a definite product. Treatment of N-acetylsarcolysine with the aminomethylthiazoles in CHCl₃ in the presence of dicyclohexylcarbodiimide (cf. loc cit.) gave N-acetylsarcolysine 2-thiazolylmethylamide, m. 174.5-5.5°, 4-thiazolylmethylamide, m. 160-1°, 2-methyl-4-thiazolylmethylamide, m. 141-2°, and 5-thiazolylamide, m. 210-11°. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Category: thiazole).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Category: thiazole

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

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles was written by Wimmer, Laurin;Parmentier, Michael;Riss, Bernard;Kapferer, Tobias;Ye, Chao;Li, Lei;Kim, Hongyong;Li, Jialiang. And the article was included in Synthesis in 2018.Reference of 80945-83-1 This article mentions the following:

The substituted 2-mercaptobenzothiazoles were prepared (by reaction of 2-haloanilines and potassium o-Et carbonodithioate) and underwent chlorination using sulfuryl chloride/water so as to yield 2-chlorobenzothiazoles such as I [X = C, N; R = H, 6-Me, 7-Cl, etc.]. This straightforward and widely used reaction was impeded due to the poor reproducibility and low reaction yields. In this protocol, it was reported that the simple addition of water to the reaction lead to remarkable improvements in reaction efficiency because of the formation of acid through partial hydrolysis of sulfuryl chloride. The observations of improved yields were also obtained in the presence of some anhydrous acidic additives, but the simple combination of sulfuryl chloride and water reproducibly provided excellent yields for a range of chlorinated products I. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole-6-carbonitrile (cas: 80945-83-1Reference of 80945-83-1).

2-Chlorobenzothiazole-6-carbonitrile (cas: 80945-83-1) 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 80945-83-1

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

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

A novel small-molecule inhibitor of IL-6 signalling was written by Zinzalla, Giovanna;Haque, Mohammad R.;Piku Basu, B.;Anderson, John;Kaye, Samantha L.;Haider, Shozeb;Hasan, Fyeza;Antonow, Dyeison;Essex, Samantha;Rahman, Khondaker M.;Palmer, Jonathan;Morgenstern, Daniel;Wilderspin, Andrew F.;Neidle, Stephen;Thurston, David E.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C4H6N2S This article mentions the following:

A small library of pyrrolidinesulfonylaryl mols., e.g. I, has been synthesized via an efficient 4-step route, and members evaluated for their ability to inhibit IL-6 signalling. One mol., I, was found to have promising activity against IL-6/STAT3 (interleukin-6/signal transducer and activator of transcription-3) signalling at the low micromolar level, and to selectively inhibit phosphorylation of STAT3 (but not STAT1) in IL-6 stimulated MDA-MB-231 breast cancer and HeLa cell lines. It was also selectively cytostatic in MDA-MB-231 (STAT3-dependent) vs. A4 (STAT3-null) cells suggesting STAT3-specific inhibitory properties. 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. 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.Formula: C4H6N2S

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