Category: 95-24-9

Ni, Qijian published the artcileOrganocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives, Computed Properties of 95-24-9, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(21), 3155-3158, database is CAplus and MEDLINE.

An organocatalytic asym. domino Mannich/cyclization reaction between 2-benzothiazolimines I (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.) with azlactones II (R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20 : 1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines III (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.; R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) bearing adjacent tertiary and quaternary stereogenic centers.

Chemical Communications (Cambridge, United Kingdom) published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Computed Properties of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhang, Zeshuai published the artcileThree-Component One-Pot Construction of 2-Aryl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidines Using Solid Calcium Carbide as a Surrogate of Gaseous Acetylene, Application In Synthesis of 95-24-9, the publication is Organic Letters (2022), 24(29), 5491-5496, database is CAplus and MEDLINE.

A concise method for the construction of 2-aryl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidines I (R = H, Cl, OMe; R¹ = Ph, naphthalen-2-yl, thiophen-2-yl, 2H-1,3-benzodioxol-5-yl, etc.) using solid calcium carbide instead of gaseous acetylene as an alkyne source and 2-aminobenzothiazoles II and aromatic aldehydes R¹CHO as substrates through one-pot three-component cascade reactions is described. The salient features for this protocol are the use of an inexpensive and easy-to-handle alkyne source, noble-metal-free condition, wide substrate scope and functional tolerance, satisfactory yield, and simple workup procedure.

Organic Letters published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C13H9FO2, Application In Synthesis of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zheng, Jun published the artcileRhodium-Catalyzed Chemo-, Regio-, and Enantioselective Allylation of 2-Aminothiazoles with Terminal Allenes, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is European Journal of Organic Chemistry (2019), 2019(31-32), 5180-5182, database is CAplus.

A rhodium-catalyzed chemo-, regio- and enantioselective intermol. coupling reaction of 2-aminobenzothiazoles with terminal allenes is reported. The new reaction displays a wide substrate scope for both reaction partners to deliver the allylation products in good yields, with excellent regio- and enantioselectivity. This novel methodol. was further applied in an efficient synthesis of chiral isothiourea.

European Journal of Organic Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C15H24S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Haroun, Michelyne published the artcileExploration of the Antimicrobial Effects of Benzothiazolylthiazolidin-4-One and In Silico Mechanistic Investigation, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Molecules (2021), 26(13), 4061, database is CAplus and MEDLINE.

Infectious diseases still affect large populations causing significant morbidity and mortality. Bacterial and fungal infections for centuries were the main factors of death and disability of millions of humans. Despite the progress in the control of infectious diseases, the appearance of resistance of microbes to existing drugs creates the need for the development of new effective antimicrobial agents. In an attempt to improve the antibacterial activity of previously synthesized compounds modifications to their structures were performed. Nineteen thiazolidinone derivatives with 6-Cl, 4-OMe, 6-CN, 6-adamantan, 4-Me, 6-adamantan substituents at benzothiazole ring were synthesized and evaluated against panel of four bacterial strains S. aureus, L. monocytogenes, E. coli and S. typhimirium and three resistant strains MRSA, E. coli and P. aeruginosa in order to improve activity of previously evaluated 6-OCF3-benzothiazole-based thiazolidinones. The evaluation of min. inhibitory and min. bactericidal concentration was determined by microdilution method. As reference compounds ampicillin and streptomycin were used. All compounds showed antibacterial activity with MIC in range of 0.12-0.75 mg/mL and MBC at 0.25->1.00 mg/mL The most active compound among all tested appeared to be compound 18, with MIC at 0.10 mg/mL and MBC at 0.12 mg/mL against P. aeruginosa. as well as against resistant strain P. aeruginosa with MIC at 0.06 mg/mL and MBC at 0.12 mg/mL almost equipotent with streptomycin and better than ampicillin. Docking studies predicted that the inhibition of LD-carboxypeptidase is probably the possible mechanism of antibacterial activity of tested compounds The best improvement of antibacterial activity after modifications was achieved by replacement of 6-OCF3 substituent in benzothiazole moiety by 6-Cl against S. aureus, MRSA and resistant strain of E. coli by 2.5 folds, while against L. monocytogenes and S. typhimirium from 4 to 5 folds.

Molecules published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wang, Lu published the artcileFacile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization, Synthetic Route of 95-24-9, the publication is Chinese Chemical Letters (2021), 32(1), 389-392, database is CAplus.

The 3-CF₃S substituted thioflavones I (R¹ = C₆H₅, 4-ClC₆H₄, 2-thienyl, etc.; R² = Br) and benzothiophenes II (R³ = C₆H₅, 4-FC₆H₄, 2-thienyl, etc.; R⁴ = 6-Me, 6-Cl, 4,6-(Cl)2, etc.) were achieved via the reactions of AgSCF₃ with methylthiolated alkynones 2-(SMe)-5-BrC₆H₃C(O)CCR¹ and alkynylthioanisoles, R⁵CCR³ (R⁵ = 4-chloro-2-(methylsulfanyl)phenyl, 5-methyl-2-(methylsulfanyl)phenyl, 2,4-difluoro-6-(methylsulfanyl)phenyl, etc.) resp., promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process involves addition of CF₃S radical to triple bond and cyclization with SMe moiety.

Chinese Chemical Letters published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C16H14O6, Synthetic Route of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Lange, Karen I. published the artcileKinetochore recruitment of the spindle and kinetochore-associated (Ska) complex is regulated by centrosomal PP2A in Caenorhabditis elegans, Computed Properties of 95-24-9, the publication is Genetics (2019), 212(2), 509-522, database is CAplus and MEDLINE.

During mitosis, kinetochore-microtubule interactions ensure that chromosomes are accurately segregated to daughter cells. RSA-1 (regulator of spindle assembly-1) is a regulatory B” subunit of protein phosphatase 2A that was previously proposed to modulate microtubule dynamics during spindle assembly. We have identified a genetic interaction between the centrosomal protein, RSA-1, and the spindle- and kinetochore-associated (Ska) complex in Caenorhabditis elegans. In a forward genetic screen for suppressors of rsa-1(or598) embryonic lethality, we identified mutations in ska-1 and ska-3. Loss of SKA-1 and SKA-3, as well as components of the KMN (KNL-1/MIS-12/NDC-80) complex and the microtubule end-binding protein EBP-2, all suppressed the embryonic lethality of rsa-1(or598). These suppressors also disrupted the intracellular localization of the Ska complex, revealing a network of proteins that influence Ska function during mitosis. In rsa-1(or598) embryos, SKA-1 is excessively and prematurely recruited to kinetochores during spindle assembly, but SKA-1 levels return to normal just prior to anaphase onset. Loss of the TPX2 homolog, TPXL- 1, also resulted in overrecruitment of SKA-1 to the kinetochores and this correlated with the loss of Aurora A kinase on the spindle microtubules. We propose that rsa-1 regulates the kinetochore localization of the Ska complex, with spindle-associated Aurora A acting as a potential mediator. These data reveal a novel mechanism of protein phosphatase 2A function during mitosis involving a centrosome-based regulatory mechanism for Ska complex recruitment to the kinetochore.

Genetics published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Computed Properties of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Gao, Kai published the artcileNanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is RSC Medicinal Chemistry (2021), 12(5), 809-818, database is CAplus and MEDLINE.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

RSC Medicinal Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Nath, Rajarshi published the artcileSynthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide, Quality Control of 95-24-9, the publication is Journal of Molecular Structure (2021), 129742, database is CAplus.

A series of I [R = H, 6-Cl, 5-O₂N, etc.] and II [R¹ = H, 4-MeO, 2-O₂N, 4-O₂N; R² = H, 5-Cl, 5-Br] were designed, synthesized and fulfilled structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), s.c. pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compound I [R = 6-Cl] showed significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED₅₀), 88.15 mg/kg (scPTZ ED₅₀) and toxic dose (TD₅₀) was found to be > 500mg/kg. In-silico studies including mol. docking study were carried out to establish the mol. interaction of potent compound I [R = 6-Cl] in both Na⁺ channel and GABA_A receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were performed to establish the drug likeness property.

Journal of Molecular Structure published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Quality Control of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Tank, Pragya published the artcileViscometric studies of Cu(II) surfactants derived from mustard oil in benzene at 303.15 K, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Tenside, Surfactants, Detergents (2019), 56(2), 158-163, database is CAplus.

The viscosity, specific viscosity, and fluidity of Cu(II) surfactant complexes derived from mustard oil with urea/thiourea/2-amino-6-chloro benzothiazole in a non-aqueous solvent has been determined at a constant temperature of 303.15 K. The results were used to determine the critical micelle concentration (CMC), soap complex-solvent interactions and the effect of chain length of the surfactant mol. on various parameters. The conclusions with regard to solute-solute and solute-solvent interaction have been discussed in terms of well-known Moulik and Jones-Dole equations. The effect of surfactant concentration on the viscosity of the solution in non-polar solvent has been discussed. The observations suggested that the structure breaking effect by the solute on the solvent mols. is more prominent above CMC as compared to below CMC after the formation of the micelles. This information plays a role in various industrial and biol. applications.

Tenside, Surfactants, Detergents published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C5H10O2S, Application of 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Zhu, Yu-Shen published the artcileIodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles, Computed Properties of 95-24-9, the publication is Chinese Chemical Letters (2022), 33(3), 1497-1500, database is CAplus.

A facile and sustainable approach for the amination of benzothiazoles I (X = H, N; R = H, 4-Cl, 5-OMe, 6-NO₂, 7-C(O)OMe; R¹ = H) with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles I (R¹ = NH₂) in up to 96% yield. A series of control experiments were performed, suggesting that a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazole I (R¹ = NH₂).

Chinese Chemical Letters published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C8H5F3O3, Computed Properties of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica