Tag: 100-200

Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel was written by Bilodeau, Mark T.;Balitza, Adrienne E.;Koester, Timothy J.;Manley, Peter J.;Rodman, Leonard D.;Buser-Doepner, Carolyn;Coll, Kathleen E.;Fernandes, Christine;Gibbs, Jackson B.;Heimbrook, David C.;Huckle, William R.;Kohl, Nancy;Lynch, Joseph J.;Mao, Xianzhi;McFall, Rosemary C.;McLoughlin, Debra;Miller-Stein, Cynthia M.;Rickert, Keith W.;Sepp-Lorenzino, Laura;Shipman, Jennifer M.;Subramanian, Raju;Thomas, Kenneth A.;Wong, Bradley K.;Yu, Sean;Hartman, George D.. And the article was included in Journal of Medicinal Chemistry in 2004.Formula: C9H6ClNS This article mentions the following:

A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been accomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Formula: C9H6ClNS).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Formula: C9H6ClNS

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

Decarbonylative C-H coupling of azoles and aryl esters: Unprecedented nickel catalysis and application to the synthesis of Muscoride A was written by Amaike, Kazuma;Muto, Kei;Yamaguchi, Junichiro;Itami, Kenichiro. And the article was included in Journal of the American Chemical Society in 2012.Computed Properties of C9H7NS This article mentions the following:

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

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.Computed Properties of C9H7NS

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

Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903 was written by Sharma, Swagat H.;Pablo, Juan Lorenzo;Montesinos, Monica Suarez;Greka, Anna;Hopkins, Corey R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Synthetic Route of C4H6N2S This article mentions the following:

The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biol. characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of I, a TRPC5 inhibitor that is active in multiple animal models of CKD. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Synthetic Route of C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Synthetic Route of C4H6N2S

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

A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries was written by Irako, Naoko;Hamada, Yasumasa;Shioiri, Takayuki. And the article was included in Tetrahedron in 1995.Reference of 55661-33-1 This article mentions the following:

(+)-2-Hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone were resp. converted to the corresponding Schiff bases derived from 2-thiazolemethanamine, 2-thiophenemethanamine, 2-furanmethanamine and benzyl amine. Alkylation of the Schiff base derivative of 2-thiazolemethanamine followed by removal of the chiral auxiliaries (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone afforded (S)-α-(phenylmethyl)-2-thiazolemethanamine [i.e., (S)-dolaphenine] in optically pure form. The method was applied to the asym. synthesis of the dolaphenine analogs also. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Reference of 55661-33-1).

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

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

Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors was written by Gahman, Timothy C.;Herbert, Mark R.;Lang, Henk;Thayer, Angie;Symons, Kent T.;Nguyen, Phan Manh;Massari, Mark E.;Dozier, Sara;Zhang, Yan;Sablad, Marciano;Rao, Tadimeti S.;Noble, Stewart A.;Shiau, Andrew K.;Hassig, Christian A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Safety of Thiazol-2-ylmethanamine This article mentions the following:

A series of imidazole containing thiadiazoles and pyrimidines has been designed and synthesized as dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated, and SAR studies led to the identification of compound I, which showed a dose dependent inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Safety of 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 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 Thiazol-2-ylmethanamine

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

Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study was written by Thanigaimalai, Pillaiyar;Konno, Sho;Yamamoto, Takehito;Koiwai, Yuji;Taguchi, Akihiro;Takayama, Kentaro;Yakushiji, Fumika;Akaji, Kenichi;Kiso, Yoshiaki;Kawasaki, Yuko;Chen, Shen-En;Naser-Tavakolian, Aurash;Schon, Arne;Freire, Ernesto;Hayashi, Yoshio. And the article was included in European Journal of Medicinal Chemistry in 2013.Application of 1826-13-7 This article mentions the following:

This work describes the design, synthesis, and evaluation of low-mol. weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(pyrrolidone-3-yl)-2-benzothiazole (I) (K_i = 4.1 nM), in which the P3 valine unit was substituted with a variety of distinct moieties. The resulting series of dipeptide-type inhibitors displayed moderate to good inhibitory activities against 3CL^pro. In particular, compounds (II) (R¹ = OMe, R² = H and R¹ = H, R² = OMe) exhibited good inhibitory activities with K_i values of 0.39 and 0.33 μM, resp. These low-mol. weight compounds are attractive leads for the further development of potent peptidomimetic inhibitors with pharmaceutical profiles. Docking studies were performed to model the binding interaction of the compound II (R¹ = OMe, R² = H) with the SARS-CoV 3CL protease. The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1′ position, (ii) a γ-lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the N-arylglycine unit and a backbone hydrogen bond donor at the S3-position. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application 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). 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 of 1826-13-7

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

Design and Synthesis of Human Immunodeficiency Virus Entry Inhibitors: Sulfonamide as an Isostere for the α-Ketoamide Group was written by Lu, Rong-Jian;Tucker, John A.;Zinevitch, Tatiana;Kirichenko, Olga;Konoplev, Vitalii;Kuznetsova, Svetlana;Sviridov, Sergey;Pickens, Jason;Tandel, Sagun;Brahmachary, Enugurthi;Yang, Yang;Wang, Jian;Freel, Stephanie;Fisher, Shelly;Sullivan, Alana;Zhou, Jiying;Stanfield-Oakley, Sherry;Greenberg, Michael;Bolognesi, Dani;Bray, Brian;Koszalka, Barney;Jeffs, Peter;Khasanov, Alisher;Ma, You-An;Jeffries, Cynthia;Liu, Changhui;Proskurina, Tatiana;Zhu, Tong;Chucholowski, Alexander;Li, Rongshi;Sexton, Connie. And the article was included in Journal of Medicinal Chemistry in 2007.Recommanded Product: 68867-17-4 This article mentions the following:

The crystal structures of many tertiary α-ketoamides reveal an orthogonal arrangement of the two carbonyl groups. Based on the hypothesis that the α-ketoamide HIV attachment inhibitor BMS 806 (formally BMS378806, 26) might bind to its gp120 target via a similar conformation, we designed and synthesized a series of analogs in which the ketoamide group is replaced by an isosteric sulfonamide group. The most potent of these analogs, 14i (I), demonstrated antiviral potency comparable to 26 in the M33 pseudotyped antiviral assay. Flexible overlay calculations of a ketoamide inhibitor with a sulfonamide inhibitor revealed a single conformation of each that gave significantly better overlap of key pharmacophore features than other conformations and thus suggest a possible binding conformation for each class. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Recommanded Product: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 68867-17-4

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

Facile generation of a library of 5-aryl-2-arylsulfonyl-1,3-thiazoles was written by Sheldrake, Peter W.;Matteucci, Mizio;McDonald, Edward. And the article was included in Synlett in 2006.Electric Literature of C9H7NS This article mentions the following:

Treatment of N,N-diformylaminomethyl aryl ketones with phosphorus pentasulfide/triethylamine in chloroform gives 5-arylthiazoles directly in good yield. The 5-aryl-1,3-thiazole core was successfully functionalized at the 2-position to yield, over two steps, a large array of 5-aryl-2-arylsulfonyl-1,3-thiazoles in a parallel fashion. 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. 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.Electric Literature of C9H7NS

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

Identification of alpha-substituted acylamines as novel, potent, and orally active mGluR5 negative allosteric modulators was written by Yoshikawa, Keita;Ohyama, Tomofumi;Takahashi, Eiki;Numajiri, Yoshitaka;Konno, Mitsuhiro;Moriyama, Masaki;Takemi, Natsumi;Kunita, Kana;Nishimura, Kazumi;Hayashi, Ryoji. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.HPLC of Formula: 89281-44-7 This article mentions the following:

This Letter describes the identification of a series of novel nonacetylenic mGluR5 neg. allosteric modulators based on the alpha-substituted acylamine structure. An initial structure-activity relationship study suggested that I and II might have good in vitro activity. When administered orally, these compounds were found to have an anxiolytic-like effect in a mouse model of stress-induced hyperthermia. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7HPLC of Formula: 89281-44-7).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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. 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.HPLC of Formula: 89281-44-7

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

The 1:2 molar adducts in the reaction of 5-phenylthiazole and dimethyl acetylenedicarboxylate was written by Maeda, Minoru;Ito, Shigeru;Kojima, Masaharu. And the article was included in Tetrahedron Letters in 1976.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

5-Phenylthiazole with MeO2CCCCO2Me in a 1:2 molar ratio at 60° for 2 hr gave three isomeric products: I (R = CO2Me, R1 = H; R = H, R1 = CO2Me) (II and III, resp.) and IV. III on heating in C6H6 at 130° for 12 hr gave 7.7% II and 32% IV, whereas II gradually isomerized at room temperature or in C6H6 at 130° to give IV. The results indicate that II and III are the initial addition products arising from the same zwitterion intermediate and that IV is produced directly from II. The isomerization of III to II and IV would proceed through the common intermediate and not by successive [1,5]-sigmatropic shifts. 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 in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.Application In Synthesis of 5-Phenylthiazole

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