Day: February 9, 2023

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

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

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

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

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

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products was written by Xu, Hui;Ma, Biao;Fu, Zunyun;Li, Han-Yuan;Wang, Xing;Wang, Zhen-Yu;Li, Ling-Jun;Cheng, Tai-Jin;Zheng, Mingyue;Dai, Hui-Xiong. And the article was included in ACS Catalysis in 2021.Name: Benzothiazole-5-carboxylic acid This article mentions the following:

A palladium-catalyzed ligand-promoted alkynation of unstrained aryl ketones RC(O)R¹ (R = naphthalen-2-yl, 1-benzothiophen-5-yl, 4-(2H-1,2,3-triazol-2-yl)benzen-1-yl, etc.; R¹ = Me, n-Pr, Ph, etc.) have been reported. The protocol allows the alkynation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope for the synthesis of aryl-/terminal alkynes RCCR² (R² = 2-fluorophenyl, naphthalen-2-yl, thiophen-2-yl, etc.) and RCCH. The potential applications of this protocol in drug discovery and chem. biol. are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products e.g., I. More importantly, two different biol. important fragments R³CCR⁴ (R = 3-methoxy-4-([(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy)benzen-1-yl, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalen-2-yl; R⁴ = 4-(dipropylsulfamoyl)phenyl) derived from a pharmaceutical and natural product could be connected by the consecutive alkynation of ketones CH₃(CH₂)₂C(O)R⁴. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone (1-[(17β)-17-(acetyloxy)estra-1,3,5(10)-trien-2-yl]ethanone) by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Name: Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. 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.Name: Benzothiazole-5-carboxylic acid

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

Second Generation Tetrahydroquinoline-Based Protein Farnesyltransferase Inhibitors as Antimalarials was written by Bendale, Pravin;Olepu, Srinivas;Suryadevara, Praveen Kumar;Bulbule, Vivek;Rivas, Kasey;Nallan, Laxman;Smart, Brian;Yokoyama, Kohei;Ankala, Sudha;Pendyala, Prakash Rao;Floyd, David;Lombardo, Louis J.;Williams, David K.;Buckner, Frederick S.;Chakrabarti, Debopam;Verlinde, Christophe L. M. J.;Van Voorhis, Wesley C.;Gelb, Michael H.. And the article was included in Journal of Medicinal Chemistry in 2007.Safety of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Substituted tetrahydroquinolines (THQs) have been previously identified as inhibitors of mammalian protein farnesyltransferase (PFT). Previously it was shown that blocking PFT in the malaria parasite led to cell death and that THQ-based inhibitors are the most potent among several structural classes of PFT inhibitors (PFTIs). THQ-based PFTIs, e.g., I, were synthesized and several compounds were discovered that inhibit the malarial enzyme in the sub- to low-nanomolar range and that block the growth of the parasite (P. falciparum) in the low-nanomolar range. This body of structure-activity data can be rationalized in most cases by consideration of the X-ray structure of one of the THQs bound to mammalian PFT together with a homol. structural model of the malarial enzyme. The results of this study provide the basis for selection of antimalarial PFTIs for further evaluation in preclin. drug discovery assays. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Safety of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Safety of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary Amines and N₁,C₅-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl Alcohols was written by Donthiri, Ramachandra Reddy;Pappula, Venkatanarayana;Chandra Mohan, Darapaneni;Gaywala, Hiren H.;Adimurthy, Subbarayappa. And the article was included in Journal of Organic Chemistry in 2013.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

In the presence of a catalytic amount of NaOH, the selective N-alkylation of various heteroaromatic primary amines is reported. E.g., in presence of NaOH in toluene, N-alkylation of 2-aminobenzothiazole with 4-ClC₆H₄CH₂OH gave 93% I. With 1 equiv of NaOH, N₁,C₅-dialkylation of 4-phenyl-2-aminothiazoles has been investigated. Reaction of in situ generated aldehyde with amine yields the N-alkylated and N₁,C₅-dialkylated products through hydride ion transformation from alc. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Recommanded Product: 4,5-Diphenylthiazol-2-amine

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

CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide was written by Li, Jiaojiao;Zhang, Yihua;Jiang, Yongwen;Ma, Dawei. And the article was included in Tetrahedron Letters in 2012.Category: thiazole This article mentions the following:

A copper-catalyzed procedure was developed for assembling benzothiazolones from Et 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Category: thiazole).

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

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles was written by Wimmer, Laurin;Parmentier, Michael;Riss, Bernard;Kapferer, Tobias;Ye, Chao;Li, Lei;Kim, Hongyong;Li, Jialiang. And the article was included in Synthesis in 2018.Synthetic Route of C7H3BrClNS This article mentions the following:

The substituted 2-mercaptobenzothiazoles were prepared (by reaction of 2-haloanilines and potassium o-Et carbonodithioate) and underwent chlorination using sulfuryl chloride/water so as to yield 2-chlorobenzothiazoles such as I [X = C, N; R = H, 6-Me, 7-Cl, etc.]. This straightforward and widely used reaction was impeded due to the poor reproducibility and low reaction yields. In this protocol, it was reported that the simple addition of water to the reaction lead to remarkable improvements in reaction efficiency because of the formation of acid through partial hydrolysis of sulfuryl chloride. The observations of improved yields were also obtained in the presence of some anhydrous acidic additives, but the simple combination of sulfuryl chloride and water reproducibly provided excellent yields for a range of chlorinated products I. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Synthetic Route of C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Synthetic Route of C7H3BrClNS

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