Tag: M.W=150-200

Qiao, Jennifer X. published the artcile4-Benzothiazole-7-hydroxyindolinyl Diaryl Ureas Are Potent P2Y₁ Antagonists with Favorable Pharmacokinetics: Low Clearance and Small Volume of Distribution, Safety of 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is ChemMedChem (2014), 9(10), 2327-2343, database is CAplus and MEDLINE.

Current antithrombotic discovery efforts target compounds that are highly efficacious in thrombus reduction with less bleeding liability than the standard of care. Preclin. data suggest that P2Y₁ antagonists may have lower bleeding liabilities than P2Y₁₂ antagonists while providing similar antithrombotic efficacy. This article describes the continuous SAR efforts in a series of 7-hydroxyindolinyl diaryl ureas. When dosed orally, 4-trifluoromethyl-7-hydroxy-3,3-dimethylindolinyl analog I was highly efficacious in a model of arterial thrombosis in rats with limited bleeding. The chem. labile CF₃ group in I was then transformed to various groups via a novel one-step synthesis, yielding a series of potent P2Y₁ antagonists. Among them, the 4-benzothiazole-substituted indolines had desirable PK properties in rats, specifically, low clearance and small volume of distribution. In addition, compound II had high i.v. exposure and modest bioavailability, giving it the best overall profile.

ChemMedChem published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Safety of 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

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

Yang, Wu published the artcileDiscovery of 4-Aryl-7-Hydroxyindoline-Based P2Y₁ Antagonists as Novel Antiplatelet Agents, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is Journal of Medicinal Chemistry (2014), 57(14), 6150-6164, database is CAplus and MEDLINE.

ADP (ADP)-mediated platelet aggregation is signaled through two distinct G protein-coupled receptors (GPCR) on the platelet surface: P2Y₁₂ and P2Y₁. Blocking P2Y₁₂ receptor is a clin. well-validated strategy for antithrombotic therapy. P2Y₁ antagonists have been shown to have the potential to provide equivalent antithrombotic efficacy as P2Y₁₂ inhibitors with reduced bleeding in preclin. animal models. Th have previously reported the discovery of a potent and orally bioavailable P2Y₁ antagonist, I. This paper describes further optimization of I by introducing 4-aryl groups at the hydroxylindoline in two series. In the neutral series, II was identified with excellent potency and desirable pharmacokinetic (PK) profile. It also demonstrated similar antithrombotic efficacy with less bleeding compared with the known P2Y₁₂ antagonist prasugrel in rabbit efficacy/bleeding models. In the basic series, III (BMS-884775) was discovered with an improved PK and liability profile over I. These results support P2Y₁ antagonism as a promising new antiplatelet target.

Journal of Medicinal Chemistry published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C9H10O4, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

Gil, D. L. published the artcileStructure-activity relations of 1,2,3-benzothiadiazoles as synergists for carbaryl against the house fly (Musca domestica), Name: Benzo[d][1,2,3]thiadiazol-5-amine, the publication is Pesticide Biochemistry and Physiology (1976), 6(4), 338-49, database is CAplus.

1,2,3-Benzothiadiazoles (I, R, R1, R2, R3 = H, halogen, NH2, OH, CN, or alkyl) and related compounds were evaluated as carbaryl [63-25-2] synergists against the housefly (M. domestica). Many of these were excellent synergists, the most active being those containing various combinations of halogen, alkyl, or alkoxy substituents in the 5- and/or 6-positions of the ring. Regression anal. on the data from 14 compounds for which substituents constants were available established that synergistic activity can be satisfactorily described by equations in terms of the hydrophobic bonding constant (π) and the homolytic free radical constant (σâ€?. The results with compounds related to the 1,2,3-benzothiadiazoles suggest that synergistic activity is associated primarily with the diazosulfide moiety.

Pesticide Biochemistry and Physiology published new progress about 1753-29-3. 1753-29-3 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Amine, name is Benzo[d][1,2,3]thiadiazol-5-amine, and the molecular formula is C6H5N3S, Name: Benzo[d][1,2,3]thiadiazol-5-amine.

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

Gil, D. L. published the artcileStructure-activity relationships of 1,2,3-benzothiadiazole insecticide synergists as inhibitors of microsomal oxidation, HPLC of Formula: 1753-29-3, the publication is Pesticide Biochemistry and Physiology (1977), 7(2), 183-93, database is CAplus.

The activities of 47 substituted 1,2,3-benzothiadiazoles (I) as inhibitors of microsomal epoxidation and/or hydroxylation in enzyme preparations from rat liver or armyworm (Spodoptera eridania) gut have been evaluated. Many were found to be effective inhibitors of microsomal oxidation, the most active being the 6-butyl [60474-26-2] and 6-propoxy [63226-45-9] derivatives with I50 values of 4.9 × 10-7 and 7.0 × 10-7 M, resp., for the epoxidation reaction. Regression anal. have established that activity of the 5-, 6-, and 5,6-substituted compounds can be satisfactorily described in equations in terms of π2, π, and σ whereas that of the 4-substituted derivatives depends on π and the steric parameter Es.

Pesticide Biochemistry and Physiology published new progress about 1753-29-3. 1753-29-3 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Amine, name is Benzo[d][1,2,3]thiadiazol-5-amine, and the molecular formula is C6H5N3S, HPLC of Formula: 1753-29-3.

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

Qi, Mei-Ling published the artcileValidated liquid chromatography method for assay of tizanidine in drug substance and formulated products, Quality Control of 30536-19-7, the publication is Analytica Chimica Acta (2003), 478(2), 171-177, database is CAplus.

A new isocratic stability indicating HPLC method for determination of tizanidine in drug substance and formulated products is described. Chromatog. separation of tizanidine from the related substances and degraded products was achieved with a Hypersil CN column (150 mm×5.0 mm, 5 μm) using a mobile phase comprising a mixture of an ion-pairing solution of heptanesulfonic acid sodium salt (HAS), methanol and acetonitrile (50:57:18 (volume/volume)) within 10 min. The flow-rate was 1.0 mL/min and detection was made at 227 nm. The method has good selectivity towards tizanidine, related substances and degraded products. Limits of quantitation for tizanidine and its synthetic intermediates were determined, ranging from 0.051 to 0.54 μg/mL. The linearity range was found to be 2-20 μg/mL (r=0.9998, n=5). Mean recovery for tizanidine from the tablets was from 99.5 to 99.8%. Precision of the method was 1.0% (n=9). The method can be used for routine anal. and the quality control of tizanidine drug substance and its formulated products.

Analytica Chimica Acta published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Quality Control of 30536-19-7.

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