Tag: 100-200

Design and synthesis of new tripeptide-type SARS-CoV 3CL protease inhibitors containing an electrophilic arylketone moiety was written by Konno, Sho;Thanigaimalai, Pillaiyar;Yamamoto, Takehito;Nakada, Kiyohiko;Kakiuchi, Rie;Takayama, Kentaro;Yamazaki, Yuri;Yakushiji, Fumika;Akaji, Kenichi;Kiso, Yoshiaki;Kawasaki, Yuko;Chen, Shen-En;Freire, Ernesto;Hayashi, Yoshio. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Name: 5-Phenylthiazole This article mentions the following:

We describe here the design, synthesis and biol. evaluation of a series of mols. toward the development of novel peptidomimetic inhibitors of SARS-CoV 3CL^pro. A docking study involving binding between the initial lead compound (I) and the SARS-CoV 3CL^pro motivated the replacement of a thiazole with a benzothiazole unit as a warhead moiety at the P1′ site. This modification led to the identification of more potent derivatives, including (II) (R¹ = R₂ = H; R¹ = OMe, R² = H; R¹ = H, R² = OMe; R¹ = NMe₂, H² = H; R¹ = H, R² = NMe2), with IC₅₀ or K_i values in the submicromolar to nanomolar range. In particular, compounds II (R¹ = R² = H; R¹ = H, R² = NMe₂) exhibited the most potent inhibitory activities, with K_i values of 4.1 and 3.1 nM, resp. The peptidomimetic compounds identified through this process are attractive leads for the development of potential therapeutic agents against SARS. The structural requirements of the peptidomimetics with potent inhibitory activities against SARS-CoV 3CL^pro may be summarized as follows: (i) the presence of a benzothiazole warhead at the S1′-position; (ii) hydrogen bonding capabilities at the cyclic lactam of the S1-site; (iii) appropriate stereochem. and hydrophobic moiety size at the S2-site and (iv) a unique folding conformation assumed by the phenoxyacetyl moiety at the S4-site. 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. 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.Name: 5-Phenylthiazole

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

Synthesis and antimitotic activity of 3- and 5-halo-substituted bis(2-aminophenyl) disulfides and corresponding N-alkyl derivatives was written by Mazzone, G.;Pappalardo, G.. And the article was included in Farmaco, Edizione Scientifica in 1977.Computed Properties of C7H4ClNOS This article mentions the following:

Benzothiazolones I (R = H, alkyl, CH2CO2Et; R1 or R2 = H, the other is Cl or F) were heated with NaOH to yield eleven resp. diphenyl disulfides II (R3 = H, alkyl, CH2CO2H). Antimitotic activity was found for II (R1 = H, R2 = Cl, R3 = Me) and II (R1 = H, R2 = F, R3 = Me). In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Computed Properties of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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. 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.Computed Properties of C7H4ClNOS

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

Differences in chemical constituents of poplar varieties with different anti-rust resistances was written by Zhu, Jingfang;Zhou, Yongbin. And the article was included in Dongbei Linye Daxue Xuebao in 2012.Name: 5-Phenylthiazole This article mentions the following:

An experiment was conducted to study the differences in fat soluble constituents in six poplar clones with different antirust resistances by ultrasonic extraction technique with petroleum ether and GC-MS anal. in order to shorten the breeding time. The six poplar clones were I108, 03-04-170, 03-04-141, 03-04-111, N177 and N195. Results show that the differences in fat soluble constituents are significant in the buds of poplar with different anti-rust resistances. The buds of N195 and N177 which resist poplar rust well contain such endemic elements as α-Caryophyllene, α-Bisabolol, and Me arachidate. Cinnamic acid, 4-Cyanophenyl-propylbenzoate, 9-Phenanthrol, Chlorodiphenylmethane, retinaldehyde, and p-Hydroxy-cinnamic acid only exist in N195, while α-cadinol, 2-Phenethyl octanoate, 9-Aminoacridine, and 1-Docosanol only exist in N177. Therefore, the differences in fat soluble constituents in poplar buds may determine the rust resistance in poplar. 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 rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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: 5-Phenylthiazole

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

Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles was written by Jin, Lvnan;Zhou, Xuan;Zhao, Yunbo;Guo, Jing;Stephan, Douglas W.. And the article was included in Organic & Biomolecular Chemistry in 2022.Electric Literature of C7H4ClNOS This article mentions the following:

The chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles were achieved using B(C₆F₅)₃, Rh₂(OAc)₄ or TfOH as the catalyst. This afforded routes to 54 benzothiazole derivatives These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Bronsted acid catalyzes. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Electric Literature of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Electric Literature of C7H4ClNOS

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

Low energy excited singlet states of some monophenyl substituted 5-membered heterocycles and their photoisomerization was written by Mehlhorn, A.;Fratev, F.;Monev, V.. And the article was included in Tetrahedron in 1981.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

The 2 low-lying singlet excited states of 14 monophenylated 5-membered heterocycles were studied with respect to their energy level ordering, the oscillator strengths of the pertinent transitions, the state wave functions, and the 1-particle d. matrixes. Two types of lowest energy singlet states were found by configuration anal. and similarity anal. One state is characterized by delocalization over the whole π system, whereas the other is locally excited at the Ph moiety. The relation between this classification and the different photoisomerization paths of the title compounds is discussed. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).

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

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

Experimental and theoretical study of the reactivity of thiazole and 4,5-dimethylthiazole towards free phenyl and substituted phenyl radicals was written by Vitry-Raymond, Jacqueline;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1963.Synthetic Route of C9H7NS This article mentions the following:

The reactivity of thiazole (I) towards free phenyl and p-nitrophenyl radicals (obtained by the thermal decomposition of Bz₂O₂ and p-nitrophenyldiazonium salts, resp.) was investigated. The results are interpreted on the basis of the radical polarization energies calculated by the mol. orbital method. I and Bz₂O₂ in a molar ratio of 55:1 heated at 80° under N, excess I removed, the residue hydrolyzed, and the mixture steam distilled gave a mixture of 52% 2- (II), 37% 5- (III), and 11% 4-phenylthiazole (IV). The crude residue from a similar run extracted with C₆H₆, the extract successively reextracted with concentrated HCl and concentrated aqueous NaOH, the acidic extract neutralized and extracted with Et₂O, and the extract evaporated yielded 8% mixture of 54-6% II, 29-31% III, and 13-17% IV; the alk. extract neutralized gave BzOH, m. 122°, and p-PhC₆H₄CO₂H, m. 114°. These results show that the steam distillation apparently caused a reduction of the yields of IV and that in all runs the decreasing order of reactivity of the various positions in I was 2 > 5 > 4. The spectroscopic analysis of the steam-distilled product showed the presence of 60% II, 24% III, and 16% IV. I treated with p-nitrodiazonium salts under the conditions described previously for the reaction with 4,5-dimethylthiazole (CA 55, 22288c) gave 14% of a mixture of 3 isomeric monosubstitution products. The electron distribution in 2-, 4-, and 5-methylthiazole and in 4,5-dimethylthiazole was calculated In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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. 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.Synthetic Route of C9H7NS

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

Pyridyl and thiazolyl bisamide CSF-1R inhibitors for the treatment of cancer was written by Scott, David A.;Aquila, Brian M.;Bebernitz, Geraldine A.;Cook, Donald J.;Dakin, Les A.;Deegan, Tracy L.;Hattersley, Maureen M.;Ioannidis, Stephanos;Lyne, Paul D.;Omer, Charles A.;Ye, Minwei;Zheng, XiaoLan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Electric Literature of C4H6N2S This article mentions the following:

The bisamide class of kinase inhibitors was identified as being active against CSF-1R. The synthesis and SAR of pyridyl and thiazolyl bisamides are reported, along with the pharmacokinetic properties and in vivo activity of selected examples. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Electric Literature of C4H6N2S).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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. 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.Electric Literature of C4H6N2S

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

Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides was written by Bilodeau, Francois;Brochu, Marie-Christine;Guimond, Nicolas;Thesen, Kris H.;Forgione, Pat. And the article was included in Journal of Organic Chemistry in 2010.Safety of 5-Phenylthiazole This article mentions the following:

A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics E.g., in presence of bis(tri-tert-butylphosphine)palladium, reaction of 1-methyl-2-pyrrolecarboxylic acid and PhBr gave 88% 1-methyl-2-phenylpyrrole. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this transformation are reported. Mechanistic evidence is also disclosed that sheds light on possible reaction pathways. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Safety of 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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 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.Safety of 5-Phenylthiazole

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

Cobalt-Catalyzed Arylation of Azole Heteroarenes via Direct C-H Bond Functionalization was written by Sezen, Bengue;Sames, Dalibor. And the article was included in Organic Letters in 2003.Reference of 1826-13-7 This article mentions the following:

We herein report a new cobalt-catalyzed method for arylation of azole heteroarenes, including thiazole, oxazole, imidazole, benzothiazole, benzoxazole, and benzimidazole. The direct arylation of thiazole and oxazole was achieved both with iodo- and bromoarenes as the aryl donors in the presence of cobalt catalyst [Co(OAc)₂/IMes] and cesium carbonate, while imidazole required the use of zinc oxide as the base. A complete reversal of arylation from C-5 to C-2 was accomplished using the bimetallic Co/Cu/IMes system. A direct comparison of the new cobalt method and the previously developed palladium protocol revealed significant differences, in terms of both chem. yield and selectivity. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Reference of 1826-13-7

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

Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature was written by Yang, Fanzhi;Koeller, Julian;Ackermann, Lutz. And the article was included in Angewandte Chemie, International Edition in 2016.Electric Literature of C9H7NS This article mentions the following:

Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Electric Literature of C9H7NS).

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. 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.Electric Literature of C9H7NS

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