Tag: 100-200

In 2011,Abonia, Rodrigo; Cortes, Edwar; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo published 《Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents》.European Journal of Medicinal Chemistry published the findings.Quality Control of Methyl 4-fluoro-3-nitrobenzoate The information in the text is summarized as follows:

Novel Me 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d]imidazole-5-carboxylates I(R = 4-Br, 4-Cl, 4-Me, 4-MeO, 4-F, 3,4,5-(MeO)3, 2-OH, 4-NMe2, 3,4-(MeO)2, H, 4-CF3, 3,4-OCH2O) and II were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products I(R = 4-Cl) and II exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI50 range of 1.15-7.33 μM and 0.167-7.59 μM, resp., and suitable LC50 with values greater than 100 μM. In the experiment, the researchers used Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Quality Control of Methyl 4-fluoro-3-nitrobenzoate)

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Quality Control of Methyl 4-fluoro-3-nitrobenzoateMethyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2008,Hall, Adrian; Bit, Rino A.; Brown, Susan H.; Chowdhury, Anita; Giblin, Gerard M. P.; Hurst, David N.; Kilford, Ian R.; Lewell, Xiao; Naylor, Alan; Scoccitti, Tiziana published 《Novel methylene-linked heterocyclic EP1 receptor antagonists》.Bioorganic & Medicinal Chemistry Letters published the findings.COA of Formula: C4H7NO2S The information in the text is summarized as follows:

We describe the SAR, in terms of heterocyclic replacements, for a series of pyrazole EP1 receptor antagonists. This study led to the identification of several aromatic heterocyclic replacements for the pyrazole in the original compound Investigation of replacements for the methylene linker uncovered disparate SAR in the thiazole and pyridine series. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1COA of Formula: C4H7NO2S)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.COA of Formula: C4H7NO2S

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2007,Palmer, Andreas Marc; Grobbel, Burkhard; Brehm, Christof; Zimmermann, Peter Jan; Buhr, Wilm; Feth, Martin Philipp; Holst, Hans Christof; Simon, Wolfgang Alexander published 《Preparation of tetrahydroimidazo[2,1-a]isoquinolines and their use as inhibitors of gastric acid secretion》.Bioorganic & Medicinal Chemistry published the findings.SDS of cas: 16982-21-1 The information in the text is summarized as follows:

A series of novel tetrahydroimidazo[2,1-a]isoquinolines was prepared based on a hetero Diels-Alder reaction between an enamine and 1,2,4-triazine as key step. A structure-activity relationship was established focusing on the influence of the substitution pattern in position 3 and 6 of the heterocycle on antisecretory activity, lipophilicity, and pKa value. Potent inhibitors of the gastric acid pump were identified. After reading the article, we found that the author used Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1SDS of cas: 16982-21-1)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) 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).SDS of cas: 16982-21-1

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Ye, Chen-Xi; Chen, Shuming; Han, Feng; Xie, Xiulan; Ivlev, Sergei; Houk, K. N.; Meggers, Eric published an article in Angewandte Chemie, International Edition. The title of the article was 《Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis》.Application In Synthesis of Methyl 3-oxovalerate The author mentioned the following in the article:

A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93% yield and with up to >99.5% ee, and follow-up conversions reveal the synthetic utility of this new method [e.g., I + N-acryloyl-1H-pyrazole → II (up to 93% yield, 92% isolated, 99% ee)]. DFT calculations elucidate the origins of the observed excellent atroposelectivity. In addition to this study using Methyl 3-oxovalerate, there are many other studies that have used Methyl 3-oxovalerate(cas: 30414-53-0Application In Synthesis of Methyl 3-oxovalerate) was used in this study.

Methyl 3-oxovalerate(cas: 30414-53-0) belongs to ketone compounds. Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups.Application In Synthesis of Methyl 3-oxovalerate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2019,European Journal of Organic Chemistry included an article by Yoshimura, Akira; Jarvi, Melissa E.; Shea, Michael T.; Makitalo, Cody L.; Rohde, Gregory T.; Yusubov, Mekhman S.; Saito, Akio; Zhdankin, Viktor V.. SDS of cas: 924-99-2. The article was titled 《Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones》. The information in the text is summarized as follows:

An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from resp. aldoximes using hypervalent iodine reagent was developed for the synthesis of 3,4-disubstituted isoxazoles I [R = n-Pr, Ph, 1-naphthyl, etc.; R1 = H, Me, Ph, etc.; R2 = H, Me]. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of products I in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallog. In the experiment, the researchers used Ethyl 3-(dimethylamino)acrylate(cas: 924-99-2SDS of cas: 924-99-2)

Ethyl 3-(dimethylamino)acrylate(cas: 924-99-2) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.SDS of cas: 924-99-2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2022,Peng, Bingfei; Ma, Jiguo; Guo, Jianhua; Gong, Yating; Wang, Ronghao; Zhang, Yi; Zeng, Jinlong; Chen, Wen-Wen; Ding, Kuiling; Zhao, Baoguo published an article in Journal of the American Chemical Society. The title of the article was 《A Powerful Chiral Super Bronsted C-H Acid for Asymmetric Catalysis》.Quality Control of tert-Butyl carbamate The author mentioned the following in the article:

A new type of chiral super Bronsted C-H acids, BINOL-derived phosphoryl bis((trifluoromethyl)sulfonyl) methanes (BPTMs) I [R = Ph, 4-NO2C6H4, 1-naphthyl, etc.] were developed. As compared to widely utilized BINOL-derived chiral phosphoric acids (BPAs) and N-triflyl phosphoramides (NTPAs), BPTMs displayed much higher Bronsted acidity, resulting in dramatically improved activity and excellent enantioselectivity as demonstrated in catalytic asym. Mukaiyama-Mannich reaction, allylic amination, three-component coupling of allyltrimethylsilane with 9-fluorenylmethyl carbamate and aldehydes, and protonation of silyl enol ether. These new strong Bronsted C-H acids have provided a platform for expanding the chem. of asym. Bronsted acid catalysis. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl carbamate(cas: 4248-19-5Quality Control of tert-Butyl carbamate)

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Quality Control of tert-Butyl carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Xiong, Jiaying; Zhuang, Tao; Ma, Yurong; Xu, Junyi; Ye, Jiaqi; Ma, Ru; Zhang, Shuang; Liu, Xin; Liu, Bi-Feng; Hao, Chao; Zhang, Guisen; Chen, Yin published an article in 2021. The article was titled 《Optimization of bifunctional piperidinamide derivatives as σ1R Antagonists/MOR agonists for treating neuropathic pain》, and you may find the article in European Journal of Medicinal Chemistry.SDS of cas: 4755-77-5 The information in the text is summarized as follows:

Described the optimization, synthesis and associated pharmacol. analgesic activities of a new series of bifunctional piperidinamide derivatives I [R1 = H, Me; R2 = H, Me, Et; R3 = H, Me, Ph etc.; R4 = Et, acetyl, cyclopropanecarbonyl etc.; R5 = 1-ethylpropyl, cyclohexyl, 4-fluorophenyl] as sigma-1 receptor (σ1R) antagonists and mu opioid receptor (MOR) agonists. The new compounds I were evaluated in-vitro in σ1R and MOR binding assays. The most promising compound I [R1 = H; R2 = Me; R3 = benzyl; R4 = propanoyl; R5 = ph] (also called HKC-126), showed superior affinities for σ1R and MOR and good selectivity to addnl. receptors related to pain. Compound I [R1 = H; R2 = Me; R3 = benzyl; R4 = propanoyl; R5 = ph] showed powerful dose-dependent analgesic effects in the acetic acid writhing test, formalin test, hot plate test and chronic constriction injury (CCI) neuropathic pain model. In contrast to an equianalgesic dose of fentanyl, compound I [R1 = H; R2 = Me; R3 = benzyl; R4 = propanoyl; R5 = ph] produced fewer opioid-like side effects, such as reward liability, respiratory depression, phys. dependence and sedation. Lastly, the pharmacokinetic properties of this drug were also acceptable and these results suggested that compound I [R1 = H; R2 = Me; R3 = benzyl; R4 = propanoyl; R5 = ph] as a mixed σ1R/MOR ligand, was potential for treating neuropathic pain.Ethyl oxalyl monochloride(cas: 4755-77-5SDS of cas: 4755-77-5) was used in this study.

Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.SDS of cas: 4755-77-5

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Saito, Masato; Kawamata, Yu; Meanwell, Michael; Navratil, Rafael; Chiodi, Debora; Carlson, Ethan; Hu, Pengfei; Chen, Longrui; Udyavara, Sagar; Kingston, Cian; Tanwar, Mayank; Tyagi, Sameer; McKillican, Bruce P.; Gichinga, Moses G.; Schmidt, Michael A.; Eastgate, Martin D.; Lamberto, Massimiliano; He, Chi; Tang, Tianhua; Malapit, Christian A.; Sigman, Matthew S.; Minteer, Shelley D.; Neurock, Matthew; Baran, Phil S. published an article in 2021. The article was titled 《N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation》, and you may find the article in Journal of the American Chemical Society.Electric Literature of C4H5ClO3 The information in the text is summarized as follows:

Herein, a rationally designed platform that provides a step toward this challenge using N-ammonium ylides e.g., acetamidotrimethylazanium-tetrafluoroboranuide as electrochem. driven oxidants for site-specific, chemoselective C(sp3)-H oxidn was presented. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors. In addition to this study using Ethyl oxalyl monochloride, there are many other studies that have used Ethyl oxalyl monochloride(cas: 4755-77-5Electric Literature of C4H5ClO3) was used in this study.

Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1.Electric Literature of C4H5ClO3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Pryde, David C.; Middya, Sandip; Banerjee, Monali; Shrivastava, Ritesh; Basu, Sourav; Ghosh, Rajib; Yadav, Dharmendra B.; Surya, Arjun published an article in 2021. The article was titled 《The discovery of potent small molecule activators of human STING》, and you may find the article in European Journal of Medicinal Chemistry.Category: esters-buliding-blocks The information in the text is summarized as follows:

The adaptor protein STING plays a major role in innate immune sensing of cytosolic nucleic acids, by triggering a robust interferon response. Despite the importance of this protein as a potential therapeutic target for serious unmet medical conditions including cancer and infectious disease there remains a paucity of STING ligands. Starting with a benzothiazinone series of weak STING activators (human EC50 ∼10μM) we identified several chemotypes with sub-micromolar STING activity across all the major protein polymorphs. An example compound I, based on an oxindole core structure, demonstrated robust on-target functional activation of STING (human EC50 185 nM) in immortalized and primary cells and a cytokine induction fingerprint consistent with STING activation. Our study has identified several related series of potent small mol. human STING activators with potential to be developed as immunomodulatory therapeutics. The experimental part of the paper was very detailed, including the reaction process of Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Category: esters-buliding-blocks)

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Category: esters-buliding-blocksMethyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Budnikov, Alexander S.; Krylov, Igor B.; Lastovko, Andrey V.; Paveliev, Stanislav A.; Romanenko, Alexander R.; Nikishin, Gennady I.; Terent’ev, Alexander O. published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《Stable and reactive diacetyliminoxyl radical in oxidative C-O coupling with β-dicarbonyl compounds and their complexes》.SDS of cas: 609-14-3 The article contains the following contents:

In the present study, the unusually stable diacetyliminoxyl radical I was presented as a ”golden mean” between transient and stable unreactive radicals. It was successfully employed as a reagent for oxidative C-O coupling with β-dicarbonyl compounds II (R = Me, Bu, chloro, benzyl) and R1C(O)CH(R2)C(O)R3 (R1 = Me, phenyl; R2 = Me, allyl, Ph, benzyl, chloro; R3 = Me, Ph, ethoxy). Using this model radical the catalytic activity of acids, bases and transition metal ions in free-radical coupling was revealed. In the experiment, the researchers used Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3SDS of cas: 609-14-3)

Ethyl 2-methyl-3-oxobutanoate(cas: 609-14-3) belongs to ketone compounds. Ketones are highly reactive, although less so than aldehydes, to which they are closely related. Much of their chemical activity results from the nature of the carbonyl group. Ketones readily undergo a wide variety of chemical reactions.SDS of cas: 609-14-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics