Tag: 100-200

In 2006,Vulpetti, Anna; Casale, Elena; Roletto, Fulvia; Amici, Raffaella; Villa, Manuela; Pevarello, Paolo published 《Structure-based drug design to the discovery of new 2-aminothiazole CDK2 inhibitors》.Journal of Molecular Graphics & Modelling published the findings.SDS of cas: 3034-22-8 The information in the text is summarized as follows:

N-(5-Bromo-1,3-thiazol-2-yl)butanamide (compound 1) was found active (IC50 = 808 nM) in a high throughput screening (HTS) for CDK2 inhibitors. By exploiting crystal structures of several complexes between CDK2 and inhibitors and applying structure-based drug design (SBDD), we rapidly discovered a very potent and selective CDK2 inhibitor 4-[(5-isopropyl-1,3-thiazol-2-yl)amino] benzenesulfonamide (compound 4, IC50 = 20 nM). The syntheses, structure-based analog design, kinases inhibition data and x-ray crystallog. structures of CDK2/inhibitor complexes are reported. The results came from multiple reactions, including the reaction of 5-Bromothiazol-2-amine(cas: 3034-22-8SDS of cas: 3034-22-8)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.SDS of cas: 3034-22-8

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

Application In Synthesis of 6-Chlorobenzothiazol-2-ylamineOn May 1, 2020 ,《Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Huddar, Srigouri; Park, Chul Min; Kim, Hyung Jun; Jang, Soojin; Lee, Sunkyung. The article conveys some information:

New therapies for treating drug-resistant pneumococcal infections are urgently needed. The novel scaffold 6-hydroxy-4-oxo-1,2-dihydro-4H-quinoline was shown to have similar efficacies against all three different serotypes of S. pneumoniae, ATCC 49617 (19F), ATCC BAA-1663 (15B), and ATCC 700904 (19A), in a resazurin-based high-throughput screen using the Korea Chem. Bank library. Further studies to identify a new lead with this scaffold, including tricyclic pyrrolo[3,2,1-ij]quinolone and pyrido[3,2,1-ij]quinolone derivatives, led to the identification of 6d, 7d and 12a. Compound 6d (IC50 = 0.92, 0.75, and 0.77μM), 7d (IC50 = 0.57, 0.66, and 0.38μM) and 12a() (IC50 = 0.27, 1.03, and 0.62μM) showed submicromolar IC50 values against 19F, 15B, and 19A, resp., and thus serve as a starting point for further optimization. While some of compounds in this series exhibited acceptable pharmacokinetic profiles in preliminary in vivo rat experiments, the most active compound 12a showed poor solubility and high plasma protein binding. Our current research efforts are focused on optimizing compounds to improve physicochem. properties as well as potency. The results came from multiple reactions, including the reaction of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Application In Synthesis of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Application In Synthesis of 6-Chlorobenzothiazol-2-ylamineThiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

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

《N-thiophenylethyl-2,2-dichloro-1-cyclopropanecarboxamides: modification of the amide part of carpropamid and examination of fungicidal activity》 was published in Journal of Pesticide Science (Tokyo, Japan) in 2009. These research results belong to Kagabu, Shinzo; Shimizu, Maiko; Mori, Masaru; Kurahashi, Yoshio; Yamaguchi, Isamu. Quality Control of 2-(2-Chlorothiazol-5-yl)acetonitrile The article mentions the following:

The synthetic route for a halo-substituted thiophenylethyl variant of blasticide carpropamid is described. First, halo-substituted acetylthiophene was homologated to thiophenylacetic acid using Pb(OAc)4 and BF3OEt2, followed by reduction to CH2CH2OH with NaBH4/I2 or BH3Me2S, and then to the azide via the tosylate. The azide was transformed to the amine using triphenylphosphine, which was then allowed to react with the corresponding acyl chloride to yield the final amide product. Fungicidal tests of 50 related products for gray mold and downy mildew on cucumber, and leaf rust and powdery mildew on wheat were conducted in 500 mg/l on pot. Many compounds showed efficacy to control these plant diseases. It should be noted that several blasticide-oriented compounds displayed high control effectiveness on downy mildew. In the experiment, the researchers used 2-(2-Chlorothiazol-5-yl)acetonitrile(cas: 865660-15-7Quality Control of 2-(2-Chlorothiazol-5-yl)acetonitrile)

2-(2-Chlorothiazol-5-yl)acetonitrile(cas: 865660-15-7) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Quality Control of 2-(2-Chlorothiazol-5-yl)acetonitrile

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

In 2016,Gogliotti, Rocco D.; Blobaum, Anna L.; Morrison, Ryan M.; Daniels, J. Scott; Salovich, James M.; Cheung, Yiu-Yin; Rodriguez, Alice L.; Loch, Matthew T.; Conn, P. Jeffrey; Lindsley, Craig W.; Niswender, Colleen M.; Hopkins, Corey R. published 《Discovery and characterization of a novel series of N-phenylsulfonyl-1H-pyrrole picolinamides as positive allosteric modulators of the metabotropic glutamate receptor 4 (mGlu4)》.Bioorganic & Medicinal Chemistry Letters published the findings.Reference of 5-Bromothiazol-2-amine The information in the text is summarized as follows:

Herein the authors report the synthesis and characterization of a novel series of N-phenylsulfonyl-1H-pyrrole picolinamides as novel pos. allosteric modulators of mGlu4. The authors detail the authors’ work towards finding Ph replacements for the core scaffold of previously reported Ph sulfonamides and Ph sulfone compounds The authors’ efforts culminated in the identification of N-(1-((3,4-dimethylphenyl)sulfonyl)-1H-pyrrol-3-yl)picolinamide as a potent PAM of mGlu4. After reading the article, we found that the author used 5-Bromothiazol-2-amine(cas: 3034-22-8Reference of 5-Bromothiazol-2-amine)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Reference of 5-Bromothiazol-2-amine

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

In 2014,Khanfar, Mohammad A.; Quinti, Luisa; Wang, Hua; Choi, Soo Hyuk; Kazantsev, Aleksey G.; Silverman, Richard B. published 《Development and characterization of 3-(arylsulfamoyl)benzamides as potent and selective SIRT2 inhibitors》.European Journal of Medicinal Chemistry published the findings.Synthetic Route of C3H3BrN2S The information in the text is summarized as follows:

Inhibitors of sirtuin-2 deacetylase (SIRT2) have been shown to be protective in various models of Huntington’s disease (HD) by decreasing polyglutamine aggregation, a hallmark of HD pathol. The present study was directed at optimizing the potency of SIRT2 inhibitors containing the neuroprotective sulfobenzoic acid scaffold and improving their pharmacol. To achieve that goal, 176 analogs were designed, synthesized, and tested in deacetylation assays against the activities of major human sirtuins SIRT1-3. This screen yielded 15 compounds with enhanced potency for SIRT2 inhibition and 11 compounds having SIRT2 inhibition equal to reference compound AK-1. The newly synthesized compounds also demonstrated higher SIRT2 selectivity over SIRT1 and SIRT3. These candidates were subjected to a dose-response bioactivity assay, measuring an increase in α-tubulin K40 acetylation in two neuronal cell lines, which yielded five compounds bioactive in both cell lines and eight compounds bioactive in at least one of the cell lines tested. These bioactive compounds were subsequently tested in a tertiary polyglutamine aggregation assay, which identified five inhibitors. ADME properties of the bioactive SIRT2 inhibitors (e.g., I) were assessed, which revealed a significant improvement of the pharmacol. properties of the new entities, reaching closer to the goal of a clin.-viable candidate. The experimental process involved the reaction of 5-Bromothiazol-2-amine(cas: 3034-22-8Synthetic Route of C3H3BrN2S)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Synthetic Route of C3H3BrN2S

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

《Facile preparation of dihydro-1,4-benzothiazine derivatives via oxidative ring-expansion of 2-aminobenzothiazoles with olefins》 was published in Chemical Communications (Cambridge, United Kingdom) in 2022. These research results belong to Sun, Qing; Bao, Xiaoguang. SDS of cas: 95-24-9 The article mentions the following:

A concise and efficient approach to prepare dihydro-1,4-benzothiazine derivatives I (R1 = H, 7-Br, 5,7-difluoro, 5-OMe, etc.; R2 = Ph, naphthalen-2-yl, ethyloxidanyl, etc.; R3 = H, Me, Ph), Et 9-cyano-3,3a,9,9a-tetrahydro-2H-benzo[b]furo[2,3-e][1,4]thiazine-6-carboxylate and Et 10-cyano-4b,10,10a,11-tetrahydrobenzo[b]indeno[2,1-e][1,4]thiazine-7-carboxylate is described via oxidative ring-expansion of 2-aminobenzothiazoles II with olefins R2CH=CHR3 under metal-free conditions. This protocol is applicable for a wide range of readily accessible 2-aminobenzothiazoles II and olefins with moderate-to-good yields. The [4+2] heteroannulation between the intermediacy of oxidative ring-opening of 2-aminobenzothiazoles II and olefins is suggested to rationalize the formation of the product. In the part of experimental materials, we found many familiar compounds, such as 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9SDS of cas: 95-24-9)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.SDS of cas: 95-24-9Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

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

《Site-Selective Thiolation of (Multi)halogenated Heteroarenes》 was written by Sandfort, Frederik; Knecht, Tobias; Pinkert, Tobias; Daniliuc, Constantin G.; Glorius, Frank. Recommanded Product: 3034-22-8 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

A general and simple strategy for the site-selective thiolation of various pharmaceutically relevant electron-rich heteroarenes with thiols is reported. This mild and reliable photocatalytic protocol enables C-S coupling at the most electron-rich position of the (multi)halogenated substrates, complementing established methodologies. Exptl. and computational studies suggest a radical chain mechanism with the key step being a homolytic aromatic substitution of the heteroaryl halide by an electrophilic thiyl radical, highlighting an underdeveloped reactivity mode. In the part of experimental materials, we found many familiar compounds, such as 5-Bromothiazol-2-amine(cas: 3034-22-8Recommanded Product: 3034-22-8)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Recommanded Product: 3034-22-8

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

The author of 《Biocatalytic dynamic reductive kinetic resolution of aryl α-chloro β-keto esters: divergent, stereocontrolled synthesis of diltiazem, clentiazem, and siratiazem》 were Yue, Xiaoping; Li, Yitong; Liu, Minjie; Sang, Di; Huang, Zedu; Chen, Fener. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2022. Product Details of 95-24-9 The author mentioned the following in the article:

The first systematic study of ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) on aryl α-chloro β-keto esters was performed and 15 structurally diverse chiral anti-aryl α-chloro β-hydroxy esters were synthesized in 74-98% isolated yields, along with moderate-to-excellent diastereoselectivity (up to >99 : 1 dr) and good-to-excellent enantioselectivity (mostly >99% ee). LfSDR1-catalyzed complete reduction of 100 g L-1 of substrate 6b at a ten-gram scale was achieved with a continuous fed-batch strategy, afforded anti-(2S,3S)-1b, the key intermediate of diltiazem, in a record-breaking space-time yield of 96 g L-1 d-1. An eight-step synthesis of diltiazem, clentiazem and siratiazem was accomplished in 32-45% overall yields, featuring this versatile biocatalytic reduction reaction as well as an efficient, green chlorination reaction in flow. In the experiment, the researchers used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Product Details of 95-24-9)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Product Details of 95-24-9The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

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

《Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds》 was published in Chemical Communications (Cambridge, United Kingdom) in 2021. These research results belong to Capaldo, Luca; Quadri, Lorenzo L.; Merli, Daniele; Ravelli, Davide. SDS of cas: 95-24-9 The article mentions the following:

A photoelectrochem. strategy for the cross-dehydrogenative coupling of unactivated aliphatic H donors (e.g. alkanes) with benzothiazoles is reported. The authors used Bu4N decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochem. scavenged the extra electrons. The experimental process involved the reaction of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9SDS of cas: 95-24-9)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.SDS of cas: 95-24-9Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

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

《Regulable cross-coupling of alcohols and benzothiazoles via a noble-metal-free photocatalyst under visible light》 was written by Pan, Zi-Tong; Qi, Xu-Kuan; Xiao, Qian; Liang, Xi-Wen; Zhong, Jian-Ji; Jian, Jing-Xin; Tong, Qing-Xiao. Recommanded Product: 95-24-9 And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022. The article conveys some information:

Two series of alkyl-derived benzothiazoles I [R = Et, iPr, cyclohexyl, etc.; R1 = H, 4-Cl, 7-Br, etc.] and acetyl-derived benzothiazoles II [R2 = Me, Et, n-Bu, etc.; R3 = H, 4-Cl, 6-Br, etc.] were synthesized via noble-metal-free photocatalyzed regulable cross-coupling reaction of benzothiazoles and alcs. with the highest isolated yields of up to 99% and 90% resp. In the experimental materials used by the author, we found 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Recommanded Product: 95-24-9)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Recommanded Product: 95-24-9Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis.

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