Tag: 100-200

Pd-Catalyzed Decarbonylative C-H Coupling of Azoles and Aromatic Esters was written by Matsushita, Kaoru;Takise, Ryosuke;Hisada, Tomoya;Suzuki, Shin;Isshiki, Ryota;Itami, Kenichiro;Muto, Kei;Yamaguchi, Junichiro. And the article was included in Chemistry – An Asian Journal in 2018.Electric Literature of C9H7NS This article mentions the following:

A decarbonylative C-H coupling of azoles and aromatic esters by palladium catalysis was described. Previously reported Ni-catalyzed C-H coupling of azoles and aromatic esters had a significant drawback regarding the substrate scope. Herein, palladium catalysis employed instead of nickel and resulted in a broader substrate scope in terms of azoles and aromatic esters. 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. 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. 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.Electric Literature of C9H7NS

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

Matrix Metalloproteinase Inhibitors: A Structure Activity Study was written by Levy, Daniel E.;Lapierre, France;Liang, Weisheng;Ye, Wenqing;Lange, Christopher W.;Li, Xiaoyuan;Grobelny, Damian;Casabonne, Marie;Tyrrell, David;Holme, Kevin;Nadzan, Alex;Galardy, Richard E.. And the article was included in Journal of Medicinal Chemistry in 1998.Name: Thiazol-2-ylmethanamine This article mentions the following:

Modifications around the dipeptide-mimetic core of hydroxamic acid based matrix metalloproteinase inhibitors I [AA = L-Trp, D-Trp, L-Trp(Me), L-3-benzothienylalanine, L-1- and -2-naphthylalanine, L-3- and -8-quinolylalanine, L-4-phenylphenylalanine, L-Phe, L-3- and -4-pyridylalanine, L–tert-leucine, L-abrine; R⁶ = NHMe, NH(CH₂)₄Me, NHCH₂CH₂OH, NHCH₂CH₂NHCO₂CH₂Ph, cyclopropylamino, cyclopentylamino, (S)- and (R)-1-indanylamino, (1R,2S)- and (1S,2R)-2-hydroxy-1-indanylamino, (S)-NHCHMePh, NHCH₂Ph, piperonylamino, 2-, 3-, and 4-pyridylmethylamino, 2-(4-pyridyl)ethylamino, NHCH₂CH₂C₆H₄OH-4, 2-furanylmethylamino, 2-thiazolylmethylamino, 2-benzimidazolylamino, 3-(1-imidazolyl)propylamino, 3-(4-morpholinyl)propylamino; R² = H, OH; R³ = CH₂CHMe₂, Bu, n-hexyl, n-octyl, OCHMe₂, O(CH₂)₄Me] were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1′ and P3′ substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess potent zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R³ as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Name: Thiazol-2-ylmethanamine).

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. 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.Name: Thiazol-2-ylmethanamine

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

Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature was written by Gandeepan, Parthasarathy;Mo, Jiayu;Ackermann, Lutz. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Reference of 1826-13-7 This article mentions the following:

Inexpensive copper catalysts enabled direct C-H chalcogenations at ambient temperature by means of photo-induced catalysis. The expedient copper catalysis set the stage for C-S and C-Se bond formation from readily accessible non-volatile elemental chalcogens. The photo-assisted copper catalysis manifold proved suitable for a wide range of substrates with good functional group tolerance and exhibited high catalytic efficacy even at a reaction temperature of 25°. 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. 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.Reference of 1826-13-7

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

Development and characterization of 3-(arylsulfamoyl)benzamides as potent and selective SIRT2 inhibitors was written by Khanfar, Mohammad A.;Quinti, Luisa;Wang, Hua;Choi, Soo Hyuk;Kazantsev, Aleksey G.;Silverman, Richard B.. And the article was included in European Journal of Medicinal Chemistry in 2014.Quality Control of Thiazol-2-ylmethanamine This article mentions the following:

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. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Quality Control of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Quality Control of Thiazol-2-ylmethanamine

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

Indolyl and dihydroindolyl N-glycinamides as potent and in vivo active NPY5 antagonists was written by Wu, Lingyun;Lu, Kai;Packiarajan, Mathivanan;Jubian, Vrej;Chandrasena, Gamini;Wolinsky, Toni C.;Walker, Mary W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Formula: C7H4ClNOS This article mentions the following:

A novel series of indolyl and dihydroindolyl glycinamides were identified as potent NPY5 antagonists with in vivo activity from screen hit I. The dihydroindolyl glycinamide II significantly inhibits NPY5 agonist induced feeding at a dose of 0.1 mg/kg. The indolyl glycinamide III also inhibits NPY5 agonist induced feeding at a dose of 1 mg/kg. Both II and III represent potential tools for further investigation into the biol. of the NPY5 receptor. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Formula: 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C7H4ClNOS

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

Nitration of thiazoles and isothiazoles. Application to 2-benzyl- and 2-phenethylthiazoles and to their mono and dimethyl derivatives. Phenylthiazoles and -isothiazoles was written by Baule, Michel;Vivaldi, Robert;Poite, Jean C.;Dou, Henri J. M.;Vernin, Gaston;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1971.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

Nitration of a series of thiazoles and isothiazoles with concentrated HNO3-H2SO4 showed strong deactivation of the Ph group due to the effect of pos. pole of the thiazole or isothiazole ring, which behaved differently. The pos. pole oriented substitution meta and para in 2-benzylthiazoles and para in 2-phenethylthiazoles. The exptl. results and calculated theoretical electronic ds. were not in good agreement. 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. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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

Antitubercular and Antiparasitic 2-Nitroimidazopyrazinones with Improved Potency and Solubility was written by Ang, Chee Wei;Tan, Lendl;Sykes, Melissa L.;AbuGharbiyeh, Neda;Debnath, Anjan;Reid, Janet C.;West, Nicholas P.;Avery, Vicky M.;Cooper, Matthew A.;Blaskovich, Mark A. T.. And the article was included in Journal of Medicinal Chemistry in 2020.Name: Thiazol-2-ylmethanamine This article mentions the following:

Following the approval of delamanid and pretomanid as new drugs to treat drug-resistant tuberculosis, there is now a renewed interest in bicyclic nitroimidazole scaffolds as a source of therapeutics against infectious diseases. We recently described a nitroimidazopyrazinone bicyclic subclass with promising antitubercular and antiparasitic activity, prompting addnl. efforts to generate analogs with improved solubility and enhanced potency. The key pendant aryl substituent was modified by (i) introducing polar functionality to the methylene linker, (ii) replacing the terminal Ph group with less lipophilic heterocycles, or (iii) generating extended biaryl side chains. Improved antitubercular and antitrypanosomal activity was observed with the biaryl side chains, with most analogs achieved 2- to 175-fold higher activity than the monoaryl parent compounds, with encouraging improvements in solubility when pyridyl groups were incorporated. This study has contributed to understanding the existing structure-activity relationship (SAR) of the nitroimidazopyrazinone scaffold against a panel of disease-causing organisms to support future lead optimization. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Name: Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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.Name: Thiazol-2-ylmethanamine

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

Alkylation of Heteroaryl Chlorides through Homolytic Aromatic Substitution by Alkyl Radicals Derived from Alkyl Formates was written by Ikeda, Yuko;Mandai, Tomoya;Yonekura, Kyohei;Shirakawa, Eiji. And the article was included in Chemistry Letters in 2021.Reference of 329794-40-3 This article mentions the following:

The alkylation of heteroaryl chlorides through a homolytic aromatic substitution (HAS) mechanism was achieved by the use of alkyl formates as alkylating agents in the presence of a tert-butoxy radical precursor, where alkyl radicals are generated from alkyl formates through hydrogen abstraction followed by β-scission with decarboxylation. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Reference of 329794-40-3).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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.Reference of 329794-40-3

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

α-ketoheterocycles as inhibitors of Leishmania mexicana cysteine protease CPB was written by Steert, Koen;Berg, Maya;Mottram, Jeremy C.;Westrop, Gareth D.;Coombs, Graham H.;Cos, Paul;Maes, Louis;Joossens, Jurgen;Van der Veken, Pieter;Haemers, Achiel;Augustyns, Koen. And the article was included in ChemMedChem in 2010.Reference of 1826-13-7 This article mentions the following:

Cysteine proteases of the papain superfamily are present in nearly all eukaryotes and also play pivotal roles in the biol. of parasites. Inhibition of cysteine proteases is emerging as an important strategy to combat parasitic diseases such as sleeping sickness, Chagas disease, and leishmaniasis. Inspired by the in vivo antiparasitic activity of the vinylsulfone-based cysteine protease inhibitors, a series of α-ketoheterocycles were developed as reversible inhibitors of a recombinant L. mexicana cysteine protease, CPB2.8. Three isoxazoles and especially one oxadiazole compound are potent reversible inhibitors of CPB2.8; however, in vitro whole-organism screening against a panel of protozoan parasites did not fully correlate with the observed inhibition of the cysteine protease. 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. 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.Reference of 1826-13-7

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

Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway was written by Prier, Christopher K.;MacMillan, David W. C.. And the article was included in Chemical Science in 2014.Category: thiazole This article mentions the following:

The direct α-heteroarylation of tertiary amines has been accomplished via photoredox catalysis to generate valuable benzylic amine pharmacophores. A variety of five- and six-membered chloroheteroarenes are shown to function as viable coupling partners for the α-arylation of a diverse range of cyclic and acyclic amines. Evidence is provided for a homolytic aromatic substitution mechanism, in which a catalytically-generated α-amino radical undergoes direct addition to an electrophilic chloroarene. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Category: thiazole).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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. 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.Category: thiazole

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