Category: thiazole

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

An economically and environmentally sustainable synthesis of 2-aminobenzothiazoles and 2-aminobenzoxazoles promoted by water was written by Zhang, Xinying;Jia, Xuefei;Wang, Jianji;Fan, Xuesen. And the article was included in Green Chemistry in 2011.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Tandem reactions of isothiocyanates (1) with 2-aminothiophenols (2), or isothiocyanates (1) with 2-aminophenols (4), were carried out rapidly and efficiently in water. A significant rate acceleration of the reaction between 1a and 2a in water compared with commonly used volatile organic solvents was observed Through these reactions, a variety of structurally and pharmaceutically interesting 2-aminobenzothiazoles (3) and 2-aminobenzoxazoles (5) were synthesized in good yields. This novel synthetic approach toward 3 and 5 has advantages such as high efficiency, readily available starting materials, environmentally benign solvent, and highly simple and practical exptl. procedures. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine

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

Photochemical synthesis of 2-substituted benzothiazoles was written by Muthusamy, Sengoden;Paramasivam, Rangasamy;Ramakrishnan, Vayalakkavoor T.. And the article was included in Journal of Heterocyclic Chemistry in 1991.Computed Properties of C13H10N2S This article mentions the following:

The photochem. cyclization of indolethiocarbanilides I (R, R¹ = H, Cl; R², R³ = H, Me; R⁴ = Cl, Br), o-ClC₆H₄NHCSNR⁵R⁶ (R⁵ = H, Ph; R⁶ = COPh, Ph) and dioxothiocyclohexanecarboxanilides II (R⁷ = H; R⁸ = H, Me; R⁷R⁸ = CH:CHCH:CH) affording the resp. benzothiazoles e.g., III, IV, V are described. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Computed Properties of C13H10N2S

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

A novel synthesis of 2-benzothiazolamine and its derivatives by a nickel(0)-catalyzed reaction of 1,2-aminoiodoarenes with thioureas was written by Takagi, Kentaro. And the article was included in Chemistry Letters in 1986.Synthetic Route of C13H10N2S This article mentions the following:

In the presence of a Ni(0) complex, 1,2-aminoiodoarenes underwent cyclization with thioureas to provide a facile, site-specific, and general synthetic procedure of 2-benzothiazolamine (I) and its derivatives under non-oxidative conditions. Thus, in the presence of catalytic amount of Ni(0) complex, generated in situ from (Et₃P)₂NiCl₂ and NaBH₃CN as a reducing agent, o-iodoaniline was treated with thiourea in DMF at 60° 20 h to give 92% I. Similarly prepared were 12 II (R = H, Me, Cl, CF₃; R¹ = H, Me, Bu, Ph; R² = H, Me). In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Synthetic Route of C13H10N2S

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

Cobalt-catalyzed domino C-N cross-coupling reaction between phenyl(2-halo)isothiourea and aryl halide was written by Kondraganti, Lakshmi;Tamminana, Ramana;Nathani, Srinivasa Rao;Babu, Manabolu Surendra;Ramachandran, Dittakavi. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2021.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A simple route for the synthesis of 2-aminophenyl benzothiazole through domino intra and inter mol. C-N cross-coupling reaction using a cobalt catalyst under mild reaction conditions has been accomplished. The procedure is exptl. simple, general, and efficient. The reaction was readily carried out under optimized reaction conditions to provide target products in moderate to good yield. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine

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

Synthesis of APTRA derivatives as building blocks for low-affinity fluorescent Ca²⁺ indicators was written by Metten, Bert;Smet, Mario;Boens, Noel;Dehaen, Wim. And the article was included in Synthesis in 2005.Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

Synthesis of trialkyl aminophenoltriacetates (APTRA triesters) and the functionalization of these into suitable building blocks for potential fully conjugated low-affinity fluorescent Ca²⁺ indicators was developed. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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 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.Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Ferulic acid and benzothiazole dimer derivatives with high binding affinity to β-amyloid fibrils was written by Byeon, Seong Rim;Jin, Yun Jung;Lim, Soo Jeong;Lee, Ji Hoon;Yoo, Kyung Ho;Shin, Kye Jung;Oh, Seung Jun;Kim, Dong Jin. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Related Products of 80945-86-4 This article mentions the following:

New ferulic acid and benzothiazole dimer derivatives were synthesized and evaluated by in vitro competition assay using [¹²⁵I]TZDM for their specific binding affinities to Aβ fibrils. In particular, one compound (I) showed the most excellent binding affinity (K_i = 0.53 nM), compared to PIB (K_i = 0.77 nM), for benzothiazole binding sites of Aβ_1-42 fibrils. This result suggests a possibility of a potential AD diagnostic probe for detection of Aβ fibrils. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Related Products of 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.Related Products of 80945-86-4

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

Mechanisms affecting the development of renal cystic disease induced by diphenylthiazole was written by Torres, Vicente E.;Berndt, Theresa J.;Okamura, Mikio;Nesbit, Julie W.;Holley, Keith E.;Carone, Frank A.;Knox, Franklyn G.;Romero, Juan C.. And the article was included in Kidney International in 1988.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

To provide information on the possible influence of hypertension or its treatment on the development of cysts in autosomal dominant polycystic kidney disease, the effects of the sodium content of the diet, DOCA-salt hypertension, renovascular hypertension, and the administration of enalapril or furosemide on the development of 2-amino-4,5-diphenylthiazole (DPT)-induced renal cystic disease were studied in rats. DOCA-salt hypertension caused vascular and glomerular lesions and proteinuria, but it did not enhance the development of cysts. Cystogenesis was enhanced in exptl. conditions where the renin-angiotensin system was activated. On the other hand, suppression of the renin-angiotensin system lessened the development of cysts. This effect might be mediated by intrarenal angiotensin II and its capacity to promote cell growth and to control the postglomerular vascular resistances and the compliance of the renal interstitium. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 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. 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 4,5-Diphenylthiazol-2-amine

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