Tag: 100-200

Exploration of novel piperazine or piperidine constructed non-covalent peptidyl derivatives as proteasome inhibitors was written by Zhuang, Rangxiao;Gao, Lixin;Lv, Xiaoqing;Xi, Jianjun;Sheng, Li;Zhao, Yanmei;He, Ruoyu;Hu, Xiaobei;Shao, Yidan;Pan, Xuwang;Liu, Shourong;Huang, Weiwei;Zhou, Yubo;Li, Jia;Zhang, Jiankang. And the article was included in European Journal of Medicinal Chemistry in 2017.SDS of cas: 55661-33-1 This article mentions the following:

A series of novel piperazine or piperidine-containing non-covalent peptidyl derivatives possessing a neopentyl-asparagine residue were designed, synthesized and evaluated as proteasome inhibitors. All target compounds were screened for their 20S proteasome chymotrypsin-like inhibitory activities, and 15 ones displayed more potent activities than carfilzomib with IC₅₀ values lower than 10 nM. Subsequently, the most potent 10 analogs were tested for their cytotoxic activities against two multiple myeloma (MM) cell lines RPMI-8226 and MM-1S. Based on these experiments, selected derivatives were further evaluated for their ex vivo and in vivo blood cell proteasome inhibitory activities. The most potential compound (I) (proteasome inhibition IC₅₀: 1.2 ± 0.1 nM) with potent anti-proliferation (IC₅₀: RPMI-8226 8.4 ± 0.8 nM; MM-1S: 6.3 ± 0.8 nM), ex vivo and in vivo activities also had a prolonged half life in plasma, which demonstrated that the enzymic stabilities of this series of compounds have been improved by constructing a six-membered ring into the peptide skeleton. All the experiments confirmed the correctness of design concept, which made this series of compounds potential leads for exploring new anti-MM drugs. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1SDS of cas: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.SDS of cas: 55661-33-1

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

Transition-Metal-Free ipso-Arylative Condensation was written by Sinclair, Geoffrey S.;Kukor, Andrew J.;Imperial, Kevin Karl G.;Schipper, Derek J.. And the article was included in Macromolecules (Washington, DC, United States) in 2020.Category: thiazole This article mentions the following:

The development of economical synthetic methods remains an important step toward the widespread use of conjugated polymers. Most well-established methods require either prefunctionalization with organometallic reagents or the use of expensive transition-metal catalysts. We have shown that 2-hydroxyalkyl- and 2-hydroxyaryl-substituted thiazole N-oxides can proceed through an ipso-arylative condensation that yields bithiazole-containing conjugated small mols. and polymers. The use of 2-hydroxyaryl substituents enables access to a wide scope of thiazole N-oxide substrates and presents an economical route to the synthesis of bithiazole-based conjugated polymers with varying phys. and electronic properties. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Absorption spectra of isomeric methyl- and phenylthiazoles and their simple and quaternary salts was written by Kornilov, M. Yu.;Aych, E. D.;Smeshko, L. I.. And the article was included in Ukrainskii Khimicheskii Zhurnal (Russian Edition) in 1973.Recommanded Product: 5-Phenylthiazole This article mentions the following:

The π-π* absorption maximum for the 2-, 4-, and 5-Me and the 2-, 4-, and 5-phenylthiazoles, their HCl salts, and the N-Me quaternary salts was determined Formation of the salt resulted in a 6-7 nm bathochromic shift for each of the methylthiazoles. The bathochromic shift was larger for 5-phenylthiazole and the quaternary salt of 4-phenylthiazole. The shifts were hypsochromic with 2-phenylthiazole. These changes are discussed in terms of steric hindrance and resonance. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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 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.Recommanded Product: 5-Phenylthiazole

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

Radical reactivity in thiazoles. III. Synthesis of aryl thiazoles and their derivatives. An analytical study was written by Varnin, G.;Aune, J. P.;Dou, H. J. M.;Metzger, J.. And the article was included in Bulletin de la Societe Chimique de France in 1967.Name: 5-Phenylthiazole This article mentions the following:

Aryl- and arylalkylthiazoles were prepared and their uv, ir, and N.M.R. spectra determined Thus, according to the method of Gabriel, thioamides were prepared by treating 0.1 mole of an amide in dioxane with 1.5/5 mole P2S5 45 min. at 40°. Formation of the resultant thioamides was followed by thin layer chromatog. using silica GF-254 and C6H6 containing 5% EtOH. The obtained thioamide was treated with 0.1 mole of the carbonyl derivative at 60°, and the reaction mixture kept 2 hrs. at 100° and acidified, and dioxane was steam distilled The resulting reaction product was neutralized and steam distilled to give the corresponding thiazole. Higher yields of thiazoles were obtained by using absolute EtOH in the presence of fused NaOAc and drops of piperidine. The α-bromoketones were prepared by treating the corresponding ketones with Br2 at 50-5° in aqueous solution in the presence of KClO4 as described by Catch and D. F. Elliot. Bromination may be also carried by the use of NaOBr, or N-bromosuccinimide. The thiazoles (I) prepared are listed in the table. The prepared thiazoles were analyzed by gas chromatog. using 10% silicone SE 30 on 60/80 mesh fire brick. The retention volume for I were given at 200° and were compared with those obtained on 5% carbowax 20 M on chromosorb P 60/80 mesh. [TABLE OMITTED] The Rf and Rm values for I were given using silica DF-5 and (1:1) C6H6-CH2Cl2 eluant mixture or Al2O3 DF-5 and 55:15 heptane-CH2Cl2 eluant mixture thin layer chromatog. The conditions were given. The uv, ir, and N.M.R. spectra were discussed. 65 references. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Name: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: 5-Phenylthiazole

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

Effect of primary amines of binuclear, noncondensed ring compounds on the growth of tubercle bacilli was written by Erlenmeyer, H.;Becker, C.;Sorkin, E.;Bloch, H.;Suter, E.. And the article was included in Helvetica Chimica Acta in 1947.Formula: C9H7NS This article mentions the following:

C.A. 41, 6925h. A systematic series of compounds similar in structure to p-H₂NC₆H₄Ph (I), with a tertiary C atom para to the NH₂ group, was prepared to test the influence of the tertiary linkage on tuberculostatic activity. The growth of tubercle bacillus in surface cultures on Lockemann medium is totally inhibited by 1-25 × 10^-7 M I. In comparison with 2 × 10^-4 M Na salicylate, I is 1600 times as effective in restricting the growth of tubercle bacillus in vitro, i.e., I has a salicylate number (SN) 1600. The selected compounds, 2-(p-aminophenyl)thiazole (II), 4-(p-aminophenyl)thiazole (III), 5-(p-aminophenyl)thiazole (IV), and the isoteric 3-(p-aminophenyl)pyridine (V), show total inhibition of Lockemann surface cultures at 2.5 × 10^-7, 5 × 10^-7, 1 × 10^-7, and 3.3 × 10^-7 M, resp., and have 800, 400, 2000, and 600 SN. The linkage relationship existing in I and the 3 thiazoles was demonstrated in the syntheses. The nitration of the corresponding phenylthiazoles with HNO₃ and H₂SO₄ at 0° gave the p-NO₂ derivative exclusively whereas nitration of BzOH yields only the m-NO₂ compound PhCSNH₂ (60 g.) and 50 g. dipolymerized BrCH₂CHO in 180 cc. absolute alc. containing 3 drops of piperidine were refluxed 10 hrs. The alc.-free reaction mixture was steam-distilled in the presence of 2 N Na₂CO₃ and the distillate was extracted with ether. Distillation of the oil from the evaporated dried extract yielded 47 g. (72%) 2-phenylthiazole, b₁₈ 125-8°, nitrated to give 80% of the corresponding 2-(p-nitrophenyl)thiazole, m. 147-8°. Reduction with Raney Ni in absolute alc. produced 2.75 g. (75%) II, m. 123-4°; Ac derivative, C₁₁H₁₀N₂OS, m. 140-1°; Bz derivative, C₁₆H₁₂N₂OS, m. 164-6°. The reduction of II gave orange crystals of 4,4′-di-2-thiazolylazoxybenzene, C₁₈H₁₂N₄OS₂, m. 234-5°. Nitration of 4-phenylthiazole produced 90% of needles of 4-(p-nitrophenyl)thiazole (VI), m. 177-8°, reduced to 83% III, m. 99-100°. As proof of structure, VI was degraded by oxidation with K₂Cr₂O₇ in H₂SO₄ to p-NO₂C₆H₄CO₂H in 62% yields. Bromination of 20 g. PhCH₂CHO in 100 cc. absolute CHCl₃ under CO₂ with 10 cc. Br 6 hrs. gave 32 g. of light-green oily PhCHBrCHO, converted according to Ger. pat. 670,131 (C.A. 33, 2909.5) with HCONH₂ and PS₅ in toluene to 14.5% 5-phenylthiazole (VII), m. 40-1°. Nitration of 2.5 g. VII gave 2.95 g. (92%) of crude nitration product, recrystallized from alc. to yellow needles of 5-(p-nitrophenyl)thiazole (VIII), C₉H₆N₂O₂S, m. 145-6°, oxidatively degraded to p-NO₂C₆H₄CO₂H. Catalytic reduction of 3.2 g. VIII with Raney Ni and recrystallization from H₂O produced 2.2 g. (80%) of colorless needles of IV, C₉H₈N₂S, m. 149.5-50.0°; BzO derivative m. 206°. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Formula: C9H7NS

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

Total Synthesis of ME1036 Starting from Readily Available Inexpensive Materials was written by Han, Zhi-Jian;Li, Yang-Bin;Yang, Lu-Xi;Song, Ai-lin;Chen, Hao;Li, Yu-Min. And the article was included in Letters in Organic Chemistry in 2015.Related Products of 55661-33-1 This article mentions the following:

This work demonstrates the effective total synthesis of a new broad-spectrum parenteral carbapenem I starting from the readily available and inexpensive N-Cbz-protected glycine amide in high yield with easy work-up under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

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. 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 55661-33-1

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

1,3-Dipolar cycloaddition reactions of thiazolium and benzothiazolium nitrogen ylides with acetylenic dipolarophiles was written by Chen, Teng Yueh;Liu, Jong Ho;Chen, Kong Ming. And the article was included in Proceedings of the National Science Council, Republic of China, Part A: Physical Science and Engineering in 1989.Recommanded Product: 1826-13-7 This article mentions the following:

Reaction of equimolar amounts of thiazolium and benzothiazolium N ylides with acetylenic dipolarophiles readily gave 1:1 cycloadducts dihydropyrrolo[2,1-b]thiazoles and -benzothiazoles. However, most of them dehydrogenated easily to fully aromatized pyrrolo[2,1-b]thiazoles and pyrrolobenzothiazole. Dihydroazepino[2,1-b]benzothiazole 1:2 cycloadducts were obtained from benzothiazolium N ylide I (R = Ph) and MeO₂CC:CCO₂Me (II). I (R = OEt) did not form the expected 1:1 cycloadducts with II. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Recommanded Product: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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: 1826-13-7

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

Persistence and transformation of the herbicides [¹⁴C]fenoxaprop-ethyl and [¹⁴C]fenthiaprop-ethyl in two prairie soils under laboratory and field conditions was written by Smith, Allan E.. And the article was included in Journal of Agricultural and Food Chemistry in 1985.Application In Synthesis of 6-Chlorobenzo[d]thiazol-2(3H)-one This article mentions the following:

The exptl. herbicidal esters fenoxaprop-ethyl (I) [66441-23-4] and fenthiaprop-ethyl (II) [95617-09-7] both underwent almost complete hydrolysis within 24 h to their resp. acids in soils with moisture contents >65% of field capacity. In air-dried soils, ester hydrolysis was considerably less. The fate of the 2 ¹⁴C-labeled esters was studied in 2 soil types under laboratory and field conditions. Each herbicide gave rise to the same transformation products in the laboratory and field studies. Fenthiaprop acid  [73519-50-3] and its corresponding transformation products, i.e., a phenetole [95617-11-1], phenol [70216-88-5], and a benzthiazolone [62266-81-3], have a soil persistence of about twice that of fenoxaprop acid and corresponding transformation products. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Application In Synthesis of 6-Chlorobenzo[d]thiazol-2(3H)-one).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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 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.Application In Synthesis of 6-Chlorobenzo[d]thiazol-2(3H)-one

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

Nickel-Catalyzed C-H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules was written by Yamamoto, Takuya;Muto, Kei;Komiyama, Masato;Canivet, Jerome;Yamaguchi, Jun-Ichiro;Itami, Ken-Ichiro. And the article was included in Chemistry – A European Journal in 2011.Category: thiazole This article mentions the following:

Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. It has been established that Ni(OAc)₂/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)₂/dppf (dppf=1,1′-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, a new protocol was discovered for the present coupling using Mg(OtBu)₂ as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodol. has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) 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. 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.Category: thiazole

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

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation was written by Liao, Jennie;Guan, Weiye;Boscoe, Brian P.;Tucker, Joseph W.;Tomlin, John W.;Garnsey, Michelle R.;Watson, Mary P.. And the article was included in Organic Letters in 2018.Related Products of 55661-33-1 This article mentions the following:

A nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)arylmethanes, e.g., I. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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.Related Products of 55661-33-1

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