Heterocyclic Building Blocks-Thiazole

Progress in synthesis of 2,2′ – dibenzothiazyl disulfide was written by Song, Yuye;Li, Zhenqiu;Xiao, Haihuan;Li, Jinghua;Huang, Caixia. And the article was included in Jingxi Shiyou Huagong Jinzhan in 2007.Application of 1843-21-6 This article mentions the following:

Several main methods to produce 2,2′ – dibenzothiazyl disulfide were described including conventional method using sodium nitrite, chlorine, sodium hypochlorite as oxidants and new method using oxygen as oxidant which had economical and environmental advantages. The two methods were compared. The former did not meet the demand of green chem. industry with high cost and heavy environmental pollution due to waste water and gas, but the latter had good prospects in the future with easy access to raw material, low cost, no pollution and the repeated use of mother liquid In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

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

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

Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid-Functionalized Ionic Liquids under Mild Conditions was written by Miao, Chengxia;Zhuang, Hongfeng;Wen, Yating;Han, Feng;Yang, Qing-Feng;Yang, Lei;Li, Zhen;Xia, Chungu. And the article was included in European Journal of Organic Chemistry in 2019.COA of Formula: C7H4N2O2S2 This article mentions the following:

Thioethers as important building blocks have been usually found in organic synthesis. Herein, a series of long chained acid-functionalized ionic liquids derived from pyrrolidine were applied for the thiolation of alcs. to synthesize different compounds containing thioether structures. This kind of ionic liquids exhibited higher efficiency than general ionic liquids based on imidazole, providing up to 99 % yield with [BsCtP][OTf] as the catalyst at room temperature for 0.25 h. The results indicated that the activities of the ionic liquids have relationship with the side chain length of ionic liquids based on pyrrolidine, anions and cations. The catalytic system had wide substrate scope and was applicable for the reaction of aromatic primary and secondary alcs. and thiols including aliphatic and aromatic thiols, benzothiazole-2-thiols and benzooxazole-2-thiols. Besides, there was no obvious change in activity of the catalyst after six runs. Thus, the catalytic system exhibited good recyclability. Addnl., carbocations should be the key intermediate and several functionalized groups of the ionic liquids have synergetic effect for the thiolation. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0COA of Formula: C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.COA of Formula: C7H4N2O2S2

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

Discovery of Quinazolines as Histamine H₄ Receptor Inverse Agonists Using a Scaffold Hopping Approach was written by Smits, Rogier A.;de Esch, Iwan J. P.;Zuiderveld, Obbe P.;Broeker, Joachim;Sansuk, Kamonchanok;Guaita, Elena;Coruzzi, Gabriella;Adami, Maristella;Haaksma, Eric;Leurs, Rob. And the article was included in Journal of Medicinal Chemistry in 2008.Product Details of 55661-33-1 This article mentions the following:

From a series of small fragments that was designed to probe the histamine H₄ receptor (H₄R), we previously described quinoxaline-containing fragments that were grown into high affinity H₄R ligands in a process that was guided by pharmacophore modeling. With a scaffold hopping exercise and using the same in silico models, we now report the identification and optimization of a series of quinazoline-containing H₄R compounds This approach led to the discovery of 6-chloro-N-(furan-3-ylmethyl)2-(4-methylpiperazin-1-yl)quinazolin-4-amine (VUF10499, 54) and 6-chloro-2-(4-methylpiperazin-1-yl)-N-(thiophen-2-ylmethyl)quinazolin-4-amine (VUF10497, 55) as potent human H₄R inverse agonists (pK_i = 8.12 and 7.57, resp.). Interestingly, both compounds also possess considerable affinity for the human histamine H₁ receptor (H₁R) and therefore represent a novel class of dual action H₁R/H₄R ligands, a profile that potentially leads to added therapeutic benefit. Compounds from this novel series of quinazolines are antagonists at the rat H₄R and were found to possess anti-inflammatory properties in vivo in the rat. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Product Details 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. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Product Details of 55661-33-1

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

Reactions of 2-aminobenzothiazoles with ethylene chlorohydrin. Molecular and crystal structure of bis[3-(2-hydroxyethyl)benzothiazol-2-ylidene]ammonium chloride was written by Makhmudov, M. K.;Ambartsumova, R. F.;Tashkhodzhaev, B.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1996.Synthetic Route of C13H10N2S This article mentions the following:

2-Aminobenzothiazoles I (R = H, Me, Et, CH₂CH₂OH, Ph) reacted with ClCH₂CH₂OH to give mainly 3-(2-chloroethyl)benzothiazolinone (II; R¹ = Cl, X = O). In the case of I (R = H), the imine II (R¹ = OH, X = NH) and the title ammonium salt (III) were also obtained. Reaction of I (R = H) with II (R¹ = Cl, X = O) gave IV. 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 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 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 C13H10N2S

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

Silver-Nitrate-Catalyzed N-Arylation of Amines and O-Arylations of Phenols and Alcohols was written by Das, Rima;Mandal, Mrinmay;Chakraborty, Debashis. And the article was included in Asian Journal of Organic Chemistry in 2013.Recommanded Product: 1843-21-6 This article mentions the following:

An efficient and general protocol for an intermol. carbon-nitrogen cross-coupling of amines, alcs., and phenols with halides was developed and the synthesis of the target compounds was achieved using silver nitrate (AgNO₃) as a catalyst and N,N-dimethylethylenediamine (N,N-DMEDA) as a ligand and potassium tert-butoxide (KOtBu) as a base under a nitrogen atm. A number of primary, secondary, and heterocyclic amines were coupled with various aryl iodides to give N-aryl derivatives in good to excellent yield. Along with this, several substituted phenols as well as alcs. were coupled with various halides under the same reactions condition to give O-arylated compounds The title compounds thus formed included N-phenylbenzenamine, 1-phenyl-1H-imidazole, 4-phenylmorpholine, 1-phenyl-2,3-indoledione, N-phenylbenzamide, (4-methylphenyl)phenyl ether, (phenoxy)benzene derivatives, methoxybenzene, aryl ethers. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

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.Recommanded Product: 1843-21-6

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

Synthesis and evaluation of andrographolide derivatives as potent anti-osteoporosis agents in vitro and in vivo was written by Zhang, Songxuan;Zhang, Yuting;Fang, Yuying;Chen, Hao;Hao, Mengjiao;Tan, Qingyun;Hu, Chen;Zhou, Huihao;Xu, Jun;Gu, Qiong. And the article was included in European Journal of Medicinal Chemistry in 2021.Formula: C4H6N2S This article mentions the following:

In this work, we found that 14-deoxy-11,12-didehydroandrographolide, a derivative of andrographolide, had greatly reduced cytotoxicity compared with andrographolide and exhibited moderate anti-osteoclastogenesis activity. Thirty compounds were synthesized by introducing anti-osteoporosis chemotypes at C-19 of 14-deoxy-11,12-didehydroandrographolide. Six of them exhibited stronger inhibition of osteoclastogenesis than andrographolide. Of note, compound I displayed the most potent activity with IC₅₀ value of 0.35μM. The expression levels of osteoclast-specific genes such as TRAcP, CTSK, NFATc1, and MMP-9 were also decreased by I treatment. Furthermore, Western blot and immunofluorescence analyses demonstrated that I inhibited osteoclast differentiation through downregulation of RANKL-induced NF-κB signaling pathway. In an ovariectomized (OVX) female mice model, I significantly ameliorated bone loss. Therefore, I exhibited promising in vivo efficacy and low toxicity, indicating its therapeutic potential for the treatment of osteoporosis. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: C4H6N2S).

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.Formula: C4H6N2S

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

Structure-activity relationship of biakamide, selective growth inhibitors under nutrient-starved condition from marine sponge was written by Ishida, Ryosuke;Matsumoto, Hirokazu;Ichii, Sayaka;Kobayashi, Motomasa;Arai, Masayoshi;Kotoku, Naoyuki. And the article was included in Chemical & Pharmaceutical Bulletin in 2019.Recommanded Product: 55661-33-1 This article mentions the following:

The tumor microenvironment is considered as one of the important targets for anticancer drug discovery. In particular, nutrient deficiency may be observed in tumor microenvironment; biakamides A-D (1-4) isolated from marine sponge Petrosaspongia sp. as growth inhibitors against cancer cells adapted to glucose-deprived conditions have potential as new drugs and tools for elucidating adaptation mechanisms to these conditions. In this paper, we investigated structure-activity relationship (SAR) of biakamide to create easily accessible analog and gain insights about participation of the substructures to growth-inhibitory activity toward development of anticancer drug. This work revealed that 14,15-dinor-biakamide C (5), which is easily accessible, has similar activity to natural biakamide C (3). In addition, detailed SAR study showed the terminal acyl chain is important for interacting with target mol. and amide part including thiazole ring has acceptability to convert structures without losing activity. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 55661-33-1).

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. 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: 55661-33-1

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

Positive and negative ion spectra of 2-aminobenzothiazole derivatives was written by Claude, S.;Duc, L.;Tabacchi, R.. And the article was included in International Journal of Mass Spectrometry and Ion Physics in 1983.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The mass spectral fragmentations under electron impact of N-phenyl-, N-(o-tolyl)-, 4-methyl-N-phenyl-, and 4-methyl-N-(o-tolyl)-2-aminobenzothiazoles have been investigated. The pos. and neg. ion spectra yielded complementary information. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Quality Control of N-Phenylbenzo[d]thiazol-2-amine

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

Design, synthesis and SAR of substituted indoles as selective TrkA inhibitors was written by Hurzy, Danielle M.;Henze, Darrell A.;Cabalu, Tamara D.;Narayan, Kartik;Heller, Amanda;Cooke, Andrew J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.COA of Formula: C4H6N2S This article mentions the following:

A series of substituted indoles were examined as selective inhibitors of tropomyosin-related kinase receptor A (TrkA), a therapeutic target for the treatment of pain. An SAR optimization campaign based on ALIS screening lead compound I is reported. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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 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.COA of Formula: C4H6N2S

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

Mass spectra of derivatives of 2-phenylaminobenzothiazole and its isomers was written by Rashkes, Ya. V.;Ambartsumova, R. F.;Saprykina, V. A.;Rozhkova, N. K.. And the article was included in Zhurnal Organicheskoi Khimii in 1981.COA of Formula: C13H10N2S This article mentions the following:

The mass spectra of I (R = H, Me, MeO, Cl, NO₂; R¹, R², R³ = H, Me), II (R-R³ = H, Me), and III (R-R³ = H, Me) were recorded. Formation of [M-R]⁺ ions was accompanied by cyclization. Loss of R¹NC and R¹NCS fragments was prominent in II. III exhibited rearrangement processes. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: C13H10N2S).

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. 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.COA of Formula: C13H10N2S

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