Category: 58759-63-0

Synthesis, characterization and evaluation of antibacterial and antifungal activity of 2-mercaptobenzothiazole and 2-mercaptobenzoxazole derivatives was written by Bhat, R.;Kumbhar, P.;Helavi, V.. And the article was included in Chemistry & Biology Interface in 2019.HPLC of Formula: 58759-63-0 This article mentions the following:

An efficient tandem route for unprecedented three component reaction involving 2-mercaptobenzoxazoles or 2-mercaptobenzothiazoles, salicylic acid and malononitrile was used for the development of new 2-mercapto-chromenopyridine derivatives I [R = H, 5-NO₂, 5-SO₃H; X = O, S]. The synthesized new derivatives I were characterized by various spectroscopic methods. In addition, compounds I were screened for in vitro antibacterial and antifungal activities against variety of bacterial and fungi strains resp. Some of the synthesized derivatives were existed to be potent antibacterial derivatives against S. aureus, E. coli, P. aeruginosa, B. subtilis, P. vulgaris and antifungal derivatives against C. coffeanum, A. niger, A. terreus and P. notatum. All these findings suggested that I [R = 5-NO₂, X = S; R = 5-SO₃H, X = O] might be further exploited as a new pharmacophore model for the development of anti-fungal agents. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0HPLC of Formula: 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.HPLC of Formula: 58759-63-0

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

Biologically active fused heterocycles from naturally occurring quinones-Part-II: synthesis of 3-substituted-9-hydroxy-10-undecyl-benzo[2′,3′,:4,5]thiazolo[2,3-b]benzimidazole-8,11-diones and their antimicrobial activity was written by Rani, T. Usha;Rao, M.S.;Reddy, V. M.. And the article was included in Indian Journal of Heterocyclic Chemistry in 1997.Application of 58759-63-0 This article mentions the following:

Title compounds were prepared by condensation of 2-mercaptobenzimidazoles with bromoembelin and then converted into their acetyl, reduced acetyl, phenazine and N-acetylphenazine derivatives The compounds have been characterized by their anal. and spectral properties. Some of these compounds exhibit moderate antimicrobial activity. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Application of 58759-63-0).

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

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

Product class 18: benzothiazoles and related compounds was written by Ulrich, H.. And the article was included in Science of Synthesis in 2002.Computed Properties of C7H4N2O2S2 This article mentions the following:

Methods for preparing benzothiazoles and related annulated thiazoles are reviewed. Preparative methods include ring-closure reactions, ring transformations, aromatization and synthesis by substituent modification. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Computed Properties of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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. 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 C7H4N2O2S2

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

Radical C-H ¹⁸F-difluoromethylation of heteroarenes with [¹⁸F]difluoromethyl heteroaryl-sulfones by visible light photoredox catalysis was written by Lemos, Agostinho Luis Pereira;Trump, Laura;Lallemand, Benedicte;Pasau, Patrick;Mercier, Joel;Lemaire, Christian;Monbaliu, Jean-Christophe;Genicot, Christophe;Luxen, Andre. And the article was included in Catalysts in 2020.Electric Literature of C7H4N2O2S2 This article mentions the following:

Six new [¹⁸F]difluoromethyl heteroaryl-sulfones ArSO₂CF[¹⁸F] [Ar = 5-methoxybenzothiazol-2-yl, N-methylbenzimidazol-2-yl, 1-phenyltetrazol-5-yl, etc.] were prepared and, based on overall radiochem. yields (RCYs), three of these reagents ArSO₂CF[¹⁸F] [6-methoxy-1,3-benzothiazol-2-yl, 6-nitro-1,3-benzothiazol-2-yl, 1-phenyltetrazol-5-yl] were selected for fully automated radiosynthesis on a FASTlab synthesizer (GE Healthcare) at high level of starting radioactivity. Subsequently, their efficiency as ¹⁸F-difluoromethylating reagents was evaluated using antiherpetic drug acyclovir as a model substrate. The results showed that introduction of mol. modifications in structure of previously reported ArSO₂CF[¹⁸F] [Ar = benzothiazol-2-yl] influenced amount of fac-Ir^III(ppy)₃ and residence time needed to ensure a complete C-H ¹⁸F-difluoromethylation process. The photocatalytic C-H ¹⁸F-difluoromethylation reaction with selected reagents was extended to other heteroarenes. Radical-trapping experiments demonstrated likely involvement of radical species in C-H ¹⁸F-difluoromethylation process. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Electric Literature of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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 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.Electric Literature of C7H4N2O2S2

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

5-Aminobenzothiazole was written by Spieler, I.;Prijs, B.. And the article was included in Helvetica Chimica Acta in 1950.Electric Literature of C7H4N2O2S2 This article mentions the following:

5-Aminobenzothiazole (I) was synthesized as the HCl salt and tested for its tuberculostatic effect. 2,5-Cl(O₂N)C₆H₃NH₂ (1 g.) was refluxed 2 hrs. with 10 ml. 85% HCHO and poured into water, precipitating 0.62 g. 2,5-Cl(O₂N)C₆H₃NHCHO (II), colorless needles, m. 179-80° (from alc.). 2,4-(O₂N)₂C₆H₃Cl (20 g.) in 40 ml. alc. was treated with 66 g. NaSH solution dropwise, stirred 1 hr., and refluxed; chilling, adding 10 g. CS₂, heating to 60-70°, and refluxing 1 hr. precipitated a resinous material which was steam-distilled to remove CS₂, filtered, and the filtrate acidified with HOAc to give 2-mercapto-5-nitrobenzothiazole (III), precipitated from NH₃ solution by HOAc in yellow crystals, m. 223° (from PhNH₂). m-O₂NC₆H₄NH₂ (5.5 g.), purified by precipitation from alc. with water, was treated in 30 ml. glacial HOAc with 6.4 g. Br, and the solution stirred, chilled with ice, and allowed to stand 2 hrs.; the HBr salt of the amine soon separated, and was filtered, dried, neutralized with NH₃ water, and washed with water to give 4 g. 2,5-Br(O₂N)C₆H₃NH₂ (IV), m. 140° (from alc.). IV (3 g.) refluxed with 30 ml. 85% HCHO 3 hrs. on the water bath and poured into water precipitated 2.1 g. 2,5-Br(O₂N)C₆H₃NHCHO (V), m. 191° (from alc.-water). To III in alc.-glacial HOAc (1:1) was added several drops 30% H₂O₂ with chilling; after 30 min. addition of an excess of water and ice precipitated 5-nitrobenzothiazole (VI), m. 158-9° (from alc.-water). III treated with KMnO₄ and dilute H₂SO₄ for 15 min. at 30-35° likewise gave VI. II (1 g.) dissolved in 20 ml. alc. on the steam bath and refluxed with 500 g. Na₂S 2-3 hrs. gave a deep red solution; the alc. was distilled off, the residue filtered, and the filtrate precipitated with dilute HCl to give 200 mg. yellow VI, m. 60-1°; 5 g. V similarly gave 2.1 g. VI. VI (1 g.) was reduced by treating it with excess SnCl₂ in concentrated HCl, adding some Sn, and warming 0.5 hr. on a steam bath; chilling precipitated the white Sn double salt of I, m. about 210°, 5 g. of which was dissolved in 50 ml. warm water, saturated with H₂S, filtered, washed, the filtrate taken to dryness, and the residue crystallized from a little water with dilute HCl to give 1.8 g. I.HCl, m. about 210°. I.HCl (3 g.) refluxed 45 min. with 2 g. molten KOAc and 12 g. Ac₂O on the steam bath, then allowed to stand 1 day, taken to dryness in vacuo, the residue extracted with absolute alc., the solution again concentrated, the residue again extracted with absolute alc., the extract filtered, concentrated, and the residue recrystallized from alc.-water gave 5-acetamidobenzothiazole, m. 188-9°. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Electric Literature of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Electric Literature of C7H4N2O2S2

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

Studies on pyrethroids. I. Synthesis of some new analogs of sumicidin was written by Xu, Hansheng;Liu, Xiufang;Yu, Tianxiang;Yu, Zhifu;Xie, Xiaotian;Zou, Zhenfu;Zhou, Minyi;Cheng, Hao;Zhang, Baixin. And the article was included in Wuhan Daxue Xuebao, Ziran Kexueban in 1987.Recommanded Product: 5-Nitrobenzothiazole-2-thiol This article mentions the following:

Title compounds I (R = e.g. benzothiazolyloxy, benzothiazolylthio, phthalimidomethoxy) (20 compounds) were prepared by esterification of 4-ClC₆H₄CH(CHMe₃)COCl with RH. I showed insecticidal and acaricidal activities. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Recommanded Product: 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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: 5-Nitrobenzothiazole-2-thiol

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

Partial reduction of 1-substituted 2,4-dinitrobenzenes was written by Schulze, Juergen;Tanneberg, Hartmut;Matschiner, Hermann. And the article was included in Zeitschrift fuer Chemie in 1980.COA of Formula: C7H4N2O2S2 This article mentions the following:

Refluxing 2,4-(O₂N)₂C₆H₃R (R = NHCN, NHCONH₂, SCN, S₂CNMe₂) with Fe and HOAc 5-10 min. gave 55-88% I (X = NH, R¹ = NH₂, OH; X = S, R¹ = NH₂, SH). In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0COA of Formula: C7H4N2O2S2).

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. 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.COA of Formula: C7H4N2O2S2

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

Radical C-H ¹⁸F-difluoromethylation of heteroarenes with [¹⁸F]difluoromethyl heteroaryl-sulfones by visible light photoredox catalysis was written by Lemos, Agostinho Luis Pereira;Trump, Laura;Lallemand, Benedicte;Pasau, Patrick;Mercier, Joel;Lemaire, Christian;Monbaliu, Jean-Christophe;Genicot, Christophe;Luxen, Andre. And the article was included in Catalysts in 2020.Electric Literature of C7H4N2O2S2 This article mentions the following:

Six new [¹⁸F]difluoromethyl heteroaryl-sulfones ArSO₂CF[¹⁸F] [Ar = 5-methoxybenzothiazol-2-yl, N-methylbenzimidazol-2-yl, 1-phenyltetrazol-5-yl, etc.] were prepared and, based on overall radiochem. yields (RCYs), three of these reagents ArSO₂CF[¹⁸F] [6-methoxy-1,3-benzothiazol-2-yl, 6-nitro-1,3-benzothiazol-2-yl, 1-phenyltetrazol-5-yl] were selected for fully automated radiosynthesis on a FASTlab synthesizer (GE Healthcare) at high level of starting radioactivity. Subsequently, their efficiency as ¹⁸F-difluoromethylating reagents was evaluated using antiherpetic drug acyclovir as a model substrate. The results showed that introduction of mol. modifications in structure of previously reported ArSO₂CF[¹⁸F] [Ar = benzothiazol-2-yl] influenced amount of fac-Ir^III(ppy)₃ and residence time needed to ensure a complete C-H ¹⁸F-difluoromethylation process. The photocatalytic C-H ¹⁸F-difluoromethylation reaction with selected reagents was extended to other heteroarenes. Radical-trapping experiments demonstrated likely involvement of radical species in C-H ¹⁸F-difluoromethylation process. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Electric Literature of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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 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.Electric Literature of C7H4N2O2S2

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

5-Aminobenzothiazole was written by Spieler, I.;Prijs, B.. And the article was included in Helvetica Chimica Acta in 1950.Electric Literature of C7H4N2O2S2 This article mentions the following:

5-Aminobenzothiazole (I) was synthesized as the HCl salt and tested for its tuberculostatic effect. 2,5-Cl(O₂N)C₆H₃NH₂ (1 g.) was refluxed 2 hrs. with 10 ml. 85% HCHO and poured into water, precipitating 0.62 g. 2,5-Cl(O₂N)C₆H₃NHCHO (II), colorless needles, m. 179-80° (from alc.). 2,4-(O₂N)₂C₆H₃Cl (20 g.) in 40 ml. alc. was treated with 66 g. NaSH solution dropwise, stirred 1 hr., and refluxed; chilling, adding 10 g. CS₂, heating to 60-70°, and refluxing 1 hr. precipitated a resinous material which was steam-distilled to remove CS₂, filtered, and the filtrate acidified with HOAc to give 2-mercapto-5-nitrobenzothiazole (III), precipitated from NH₃ solution by HOAc in yellow crystals, m. 223° (from PhNH₂). m-O₂NC₆H₄NH₂ (5.5 g.), purified by precipitation from alc. with water, was treated in 30 ml. glacial HOAc with 6.4 g. Br, and the solution stirred, chilled with ice, and allowed to stand 2 hrs.; the HBr salt of the amine soon separated, and was filtered, dried, neutralized with NH₃ water, and washed with water to give 4 g. 2,5-Br(O₂N)C₆H₃NH₂ (IV), m. 140° (from alc.). IV (3 g.) refluxed with 30 ml. 85% HCHO 3 hrs. on the water bath and poured into water precipitated 2.1 g. 2,5-Br(O₂N)C₆H₃NHCHO (V), m. 191° (from alc.-water). To III in alc.-glacial HOAc (1:1) was added several drops 30% H₂O₂ with chilling; after 30 min. addition of an excess of water and ice precipitated 5-nitrobenzothiazole (VI), m. 158-9° (from alc.-water). III treated with KMnO₄ and dilute H₂SO₄ for 15 min. at 30-35° likewise gave VI. II (1 g.) dissolved in 20 ml. alc. on the steam bath and refluxed with 500 g. Na₂S 2-3 hrs. gave a deep red solution; the alc. was distilled off, the residue filtered, and the filtrate precipitated with dilute HCl to give 200 mg. yellow VI, m. 60-1°; 5 g. V similarly gave 2.1 g. VI. VI (1 g.) was reduced by treating it with excess SnCl₂ in concentrated HCl, adding some Sn, and warming 0.5 hr. on a steam bath; chilling precipitated the white Sn double salt of I, m. about 210°, 5 g. of which was dissolved in 50 ml. warm water, saturated with H₂S, filtered, washed, the filtrate taken to dryness, and the residue crystallized from a little water with dilute HCl to give 1.8 g. I.HCl, m. about 210°. I.HCl (3 g.) refluxed 45 min. with 2 g. molten KOAc and 12 g. Ac₂O on the steam bath, then allowed to stand 1 day, taken to dryness in vacuo, the residue extracted with absolute alc., the solution again concentrated, the residue again extracted with absolute alc., the extract filtered, concentrated, and the residue recrystallized from alc.-water gave 5-acetamidobenzothiazole, m. 188-9°. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Electric Literature of C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Electric Literature of C7H4N2O2S2

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

Studies on pyrethroids. I. Synthesis of some new analogs of sumicidin was written by Xu, Hansheng;Liu, Xiufang;Yu, Tianxiang;Yu, Zhifu;Xie, Xiaotian;Zou, Zhenfu;Zhou, Minyi;Cheng, Hao;Zhang, Baixin. And the article was included in Wuhan Daxue Xuebao, Ziran Kexueban in 1987.Recommanded Product: 5-Nitrobenzothiazole-2-thiol This article mentions the following:

Title compounds I (R = e.g. benzothiazolyloxy, benzothiazolylthio, phthalimidomethoxy) (20 compounds) were prepared by esterification of 4-ClC₆H₄CH(CHMe₃)COCl with RH. I showed insecticidal and acaricidal activities. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Recommanded Product: 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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: 5-Nitrobenzothiazole-2-thiol

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