October 2022 - Page 76 of 122 - Heterocyclic Building Blocks-Thiazole

Alaklab, Abdullah’s team published research in Monatshefte fuer Chemie in 2017-02-28 | 1003-32-3

Monatshefte fuer Chemie published new progress about Antibacterial agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Safety of Thiazole-5-carboxyaldehyde.

Alaklab, Abdullah; Surendra Kumar, Radhakrishnan; Ahamed, Anis; Arif, Ibrahim A.; Manilal, Aseer; Idhayadhulla, Akbar published the artcile< Synthesis of novel three compound imidazole derivatives via Cu(II) catalysis and their larvicidal and antimicrobial activities>, Safety of Thiazole-5-carboxyaldehyde, the main research area is imidazole Mannich base preparation antifungal larvicidal antibacterial.

One-pot three-component reactions of 1-[[2-(furan-2-ylmethylene)hydrazinyl](phenyl)methyl]-1H-imidazole and other imidazole derivatives were synthesized by Mannich base method in the presence of Cu(II) catalysis. Cu(Phen)Cl2 catalysis was performed well compared with other Cu(II) catalysis. Synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectra, and elemental anal. Synthesized compounds were evaluated by antimicrobial and larvicidal activities. 4-[[2-(Furan-2-ylmethylene)hydrazinyl](1H-imidazol-1-yl)methyl]-N,N-dimethylaniline was highly active (MIC: 0.5 μg/cm3) against Staphylococcus aureus compared with standard ciprofloxacin in antibacterial screening. 1-[(4-Chlorophenyl)[2-(furan-2-ylmethylene)hydrazinyl]methyl]-1H-imidazole was highly active (MIC: 0.25 μg/cm3) against Candida albicans compared with standard clotrimazole (MIC: 0.5 μg/cm3) in antifungal screening. Larvicidal activity was assessed to the urban mosquito, Culex quinquefasciatus, using a standard bioassay protocol. 1-[1-[2-(Furan-2-ylmethylene)hydrazinyl]-4,8-dimethylnona-3,7-dienyl]-1H-imidazole showed high toxicity levels of larvicidal activity based their half maximal LD (LD50) values. Therefore, some compounds are lead mols. for the growth of new classes of antimicrobial and larvicidal agents.

Monatshefte fuer Chemie published new progress about Antibacterial agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Safety of Thiazole-5-carboxyaldehyde.

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

Gromek, Samantha M’s team published research in Bioorganic & Medicinal Chemistry in 2016-11-01 | 57493-24-0

Bioorganic & Medicinal Chemistry published new progress about Antiproliferative agents. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, SDS of cas: 57493-24-0.

Gromek, Samantha M.; deMayo, James A.; Maxwell, Andrew T.; West, Ashley M.; Pavlik, Christopher M.; Zhao, Ziyan; Li, Jin; Wiemer, Andrew J.; Zweifach, Adam; Balunas, Marcy J. published the artcile< Synthesis and biological evaluation of santacruzamate A analogues for anti-proliferative and immunomodulatory activity>, SDS of cas: 57493-24-0, the main research area is santacruzamate A analog preparation antiproliferative immunomodulator; Anti-proliferative activity; Enzyme assays; Immune modulation; Natural product analogues; Santacruzamate A.

Santacruzamate A (SCA) is a natural product isolated from a Panamanian marine cyanobacterium, previously reported to have potent and selective histone deacetylase (HDAC) activity. To optimize the enzymic and cellular activity, 40 SCA analogs were synthesized in a systematic exploration of the zinc-binding group (ZBG), cap terminus, and linker region. Two cap group analogs inhibited proliferation of MCF-7 breast cancer cells, with analogous increased degranulation of cytotoxic T cells (CTLs), while one cap group analog reduced CTL degranulation, indicative of suppression of the immune response. Addnl. testing of these analogs resulted in reevaluation of the previously reported SCA mechanism of action. These analogs and the resulting structure-activity relationships will be of interest for future studies on cell proliferation and immune modulation.

Bioorganic & Medicinal Chemistry published new progress about Antiproliferative agents. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, SDS of cas: 57493-24-0.

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

Doughty, Michael B’s team published research in Journal of the Chemical Society, Chemical Communications in 1985-11-15 | 20582-55-2

Journal of the Chemical Society, Chemical Communications published new progress about Benzoin condensation reaction catalysts. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, HPLC of Formula: 20582-55-2.

Doughty, Michael B.; Risinger, G. E. published the artcile< Studies on the aminopyrimidinyl group of thiamine>, HPLC of Formula: 20582-55-2, the main research area is aminopyrimidinyl group thiamine catalytic activity; catalyst thiamine benzoin condensation.

The thiazolium salt I, when refluxed with excess PhCHO in MeOH containing 2 equivalent Et3N yielded benzoin, as did the tricyclic form of thiamine II [R = (CH2)2OH], generated in basic EtOH from thiamine.HCl and NaOEt. In contrast, although the thiamine analog III underwent a rapid C-2 H/D exchange in acidic D2O, formation of its neutral tricyclic form II (R = CO2Et) (IV) in basic solution completely inhibited its ability to catalyze the benzoin condensation. These results are discussed in terms of the intramol. cyclization to form IV and the balance between the nucleophilicity of the aminopyrimidinyl group towards the C-2 position of the thiamine thiazolium ring, and the leaving group potential of the aminopyrimidinyl moiety.

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

Gorji, Samareh’s team published research in Journal of Molecular Structure in 2021-05-05 | 57493-24-0

Journal of Molecular Structure published new progress about Alkynes, aryl Role: RCT (Reactant), RACT (Reactant or Reagent). 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, Synthetic Route of 57493-24-0.

Gorji, Samareh; Ghorbani-Vaghei, Ramin; Alavinia, Sedigheh published the artcile< Sodium alginate: Biopolymeric catalyst for the synthesis of 2-amino-4-arylthiazole derivatives in aqueous medium>, Synthetic Route of 57493-24-0, the main research area is aryl alkyne thiourea sodium alginate catalyst heterocyclization; amino arylthiazole preparation green chem.

An efficient and recoverable bifunctional heterogeneous organocatalyst for the synthesis of 2-amino-4-arylthiazole derivatives was carried out by the reaction of substituted Ph acetylene and thiourea in an eco-friendly condition in the presence of TBBDA. Mild reaction conditions, simple reaction procedure, easy purification, high yields of products, eco-friendly catalyst usage and convenient reusability were the highlighted points of this protocol.

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

Zheng, Sheng’s team published research in Nanomedicine (New York, NY, United States) in 2020-10-31 | 2591-17-5

Nanomedicine (New York, NY, United States) published new progress about Anesthesia. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Application In Synthesis of 2591-17-5.

Zheng, Sheng; Zhang, Ying; Chen, Shujie; Zhang, Zeyu; Chen, Fei; Zhang, Zizhen; Hu, Zhenhua; Tian, Jie; Wang, Liangjing published the artcile< A preliminary study of dual-band confocal laser endomicroscopy combined with image mosaic in the diagnosis of liver cancer>, Application In Synthesis of 2591-17-5, the main research area is diagnosis liver cancer confocal laser endomicroscopy; Confocal laser endomicroscopy; Fluorescein sodium; Image mosaic; Indocyanine green; Primary liver cancer; Tumor margin.

Accurate identification of tumor tissues and their margins are still challenging for conventional clin. imaging methods during liver cancer surgery. In this study, dual-band confocal laser endomicroscopy (CLE) combined with image mosaic was used to guide liver cancer surgery. In the experiments with mice bearing orthotropic liver tumor, CLE can accurately detect the tumors and identify their margins with two excitation wavelengths of 488 nm and 660 nm by clin. available dyes fluorescein sodium (FS) or indocyanine green (ICG). The mosaic CLE images enlarged the imaging field and detected the liver tumor margins more accurately. Normal liver tissues fluorescence intensity of CLE images was significantly higher than that of tumor tissues in the same tumor-bearing mice (P < 0.0001). Overall, dual-band CLE imaging demonstrates to be a promising method to identify liver tumor tissues and margins, which has the prospect of clin. application and helps to achieve intraoperative radical resection. Nanomedicine (New York, NY, United States) published new progress about Anesthesia. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Application In Synthesis of 2591-17-5.

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

Kallur, H. J.’s team published research in World Journal of Pharmaceutical Research in 2020 | CAS: 95-24-9

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Application of 95-24-9Their presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

The author of 《Synthesis, characterization and anthelmintic screening of some new benzothiophene derivatives》 were Kallur, H. J.; Mathapati, Prabhudev S.; C., Kishore Singh; Malpani, Ashok. And the article was published in World Journal of Pharmaceutical Research in 2020. Application of 95-24-9 The author mentioned the following in the article:

The proposed work was carried out by following Schemes. In the Scheme-I the starting material cinnamic acid was reacted with thionyl chloride, in presence of pyridine in chlorobenzene medium to yield 3- chlorobenzo[b]thiophene-2-carbonylchloride. Where as in the Scheme-II the 2-amino-6-substituted benzothiazoles I (R = Me, COOEt, Cl, OMe, F, nitro) was prepared by the reaction of 4-substituted anilines 4-RC6H4NH2 and potassium thiocyanate in presence of bromine in acetic acid. In the scheme-III, the compound N-(6-substituted-1,3-benzothiazol-2-yl)-3-chloro-1-benzothiophene-2-carboxamides II was prepared by reacting 3-chlorobenzo[b]thiophene-2-carbonylchloride and 2-amino-6-substituted benzothiazoles I in pyridine medium refluxed for 10-15 h. The synthesized compounds II were evaluated for the anthelmintic activity. In the part of experimental materials, we found many familiar compounds, such as 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Application of 95-24-9)

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

Kitagawa, Tokujiro’s team published research in Chemical & Pharmaceutical Bulletin in 2001 | CAS: 3034-22-8

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Category: thiazole

In 2001,Kitagawa, Tokujiro; Akiyama, Naohiro; Masai, Katsunori published 《Preparation and root growth-modulatory activity of N-substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides》.Chemical & Pharmaceutical Bulletin published the findings.Category: thiazole The information in the text is summarized as follows:

N-Substituted 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides were synthesized through the reaction of amines with 2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanoic acid, which was prepared via condensation of 2-(bromomethyl)furan with di-Et acetamidomalonate, followed by partial hydrolysis of the resultant di-Et ester in the presence of barium hydroxide. However, bulky amines such as tert-butylamine or 2-trifluoromethylaniline did not afford the corresponding diamides. The biol. activity of the prepared diamides as root growth modulators was examined by germination assay using rape and leek seeds. N-(5-Bromo-2-thiazolyl)- and N-(4-chloro-2-benzothiazolyl)-2-acetylamino-2-ethoxycarbonyl-3-(2-furyl)propanamides both potently inhibited the root growth of rape seedlings, but were less effective in the case of leek seeds. The herbicide 2,4-dichlorophenoxyacetic acid completely inhibited root growth in both cases. The results came from multiple reactions, including the reaction of 5-Bromothiazol-2-amine(cas: 3034-22-8Category: thiazole)

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

Razus, Alexandru C.’s team published research in Journal of Heterocyclic Chemistry in 2003 | CAS: 3034-22-8

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Reference of 5-Bromothiazol-2-amine

In 2003,Razus, Alexandru C.; Birzan, Liviu; Nae, Stefania; Surugiu, Mirela Nina; Cimpeanu, Valentin published 《Azulene-1-azo-2′-thiazoles. Synthesis and properties》.Journal of Heterocyclic Chemistry published the findings.Reference of 5-Bromothiazol-2-amine The information in the text is summarized as follows:

Several derivatives belonging to a new compound class, namely azulene-1-azo-2′-thiazoles, were prepared by the diazotization of 2-aminothiazoles in the presence of HNO3/H3PO4 followed by the coupling of diazonium salts with azulenes in buffered medium. The reactions proved to be general for this class, with the yields being considerably influenced by the thiazole substituents. For the first time a N-oxide of an amino-substituted five-membered nitrogen heterocycle was diazotized and coupled. The structure of the obtained azo dyes was assigned and their physico-chem. properties were discussed. The new azulene azo derivatives exhibit a strong bathochromic shift in their UV-visible spectra due to the intense push-pull effect of the azulene aromatic system and the intrinsic properties of the thiazole moiety. In the part of experimental materials, we found many familiar compounds, such as 5-Bromothiazol-2-amine(cas: 3034-22-8Reference of 5-Bromothiazol-2-amine)

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

Kitagawa, Tokujiro’s team published research in Chemical & Pharmaceutical Bulletin in 2005 | CAS: 3034-22-8

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.HPLC of Formula: 3034-22-8

In 2005,Kitagawa, Tokujiro; Asada, Makoto published 《Preparation and root growth-inhibitory activity of N-substituted 2-(2-chloroacetamido)-3-(furan-2-yl)propanamides》.Chemical & Pharmaceutical Bulletin published the findings.HPLC of Formula: 3034-22-8 The information in the text is summarized as follows:

A series of N-substituted 2-(2-chloroacetamido)-3-(furan-2-yl)propanamides, e.g., I, was prepared through the reaction of chloroacetyl chloride with N-substituted 2-amino-3-(furan-2-yl)propanamides, which were obtained by condensation of 2-(tert-butoxycarbonylamido)-3-(furan-2-yl)propanoic acid (Boc-furylalanine) with amines, followed by hydrolysis of the resultant N-substituted Boc-furylalanine acid amides in the presence of HCl/dioxane. The biol. activity of the prepared compounds as root growth inhibitors was examined by germination assay using rape seed. At the concentration of 5.0 × 10-5 M, the most active compound, 2-(2-chloroacetamido)-N-(2,6-diethylphenyl)-3-(furan-2-yl)propanamide (I), showed potent root growth-inhibitory activity of 76% towards rape seedlings. After reading the article, we found that the author used 5-Bromothiazol-2-amine(cas: 3034-22-8HPLC of Formula: 3034-22-8)

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

Li, Ningning’s team published research in Bioorganic & Medicinal Chemistry Letters in 2014 | CAS: 3034-22-8

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Synthetic Route of C3H3BrN2S

In 2014,Li, Ningning; Xu, Yintong; Xia, Qiang; Bai, Cuigai; Wang, Taiyi; Wang, Lei; He, Dingdi; Xie, Nannan; Li, Lixin; Wang, Jing; Zhou, Hong-Gang; Xu, Feng; Yang, Cheng; Zhang, Quan; Yin, Zheng; Guo, Yu; Chen, Yue published 《Simplified captopril analogues as NDM-1 inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.Synthetic Route of C3H3BrN2S The information in the text is summarized as follows:

Captopril is a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 μM. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, the authors synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors to identify the pharmacophore for NDM-1 inhibition. The authors found that the lead compound(R)-N-benzyl-3-mercapto-2-methylpropanamide had an IC50 value of 1.0 μM. Further structure simplification provided compounds 3-mercapto-2-methylpropan-1-ol and 2,3-dimercaptopropan-1-ol, which had IC50 values of 15 and 10 μM, resp. As 2,3-dimercaptopropan-1-ol is a clin. used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections.5-Bromothiazol-2-amine(cas: 3034-22-8Synthetic Route of C3H3BrN2S) was used in this study.

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