Tag: 100-200

《New activators of eIF2α Kinase Heme-Regulated Inhibitor (HRI) with improved biophysical properties》 was written by Zhang, Qingwen; Du, Ronghui; Reis Monteiro dos Santos, Guilherme Rodrigo; Yefidoff-Freedman, Revital; Bohm, Andrew; Halperin, Jose; Chorev, Michael; Aktas, Bertal H.. COA of Formula: C6H13NO And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

Heme-regulated inhibitor (HRI), a eukaryotic translation initiation factor 2 alpha (eIF2α) kinase, is critically important for coupling protein synthesis to heme availability in reticulocytes and adaptation to various environmental stressors in all cells. HRI modifies the severity of several Hb misfolding disorders including β-thalassemia. Small mol. activators of HRI are essential for studying normal- and patho-biol. of this kinase as well as for the treatment of various human disorders for which activation of HRI or phosphorylation of eIF2α may be beneficial. We previously reported development of 1-((1,4-trans)-4-aryloxycyclohexyl)-3-arylureas (cHAUs) as specific HRI activators and demonstrated their potential as mol. probes for studying HRI biol. and as lead compounds for treatment of various human disorders. To develop more druglike cHAUs for in vivo studies and drug development and to expand the chem. space, we undertook bioassay guided structure-activity relationship studies replacing cyclohexyl ring with various 4-6-membered rings and explored further substitutions on the N-Ph ring. We tested all analogs in the surrogate eIF2α phosphorylation and cell proliferation assays, and a subset of analogs in secondary mechanistic assays that included endogenous eIF2α phosphorylation and expression of C/EBP homologous protein (CHOP), a downstream effector. Finally, we determined specificity of these compounds for HRI by testing their anti-proliferative activity in cells transfected with siRNA targeting HRI or mock. These compounds have significantly improved cLogPs with no loss of potencies, making them excellent candidates for lead optimization for development of investigational new drugs that potently and specifically activate HRI.trans-4-Aminocyclohexanol(cas: 27489-62-9COA of Formula: C6H13NO) was used in this study.

trans-4-Aminocyclohexanol(cas: 27489-62-9) 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.COA of Formula: C6H13NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Journal of the American Chemical Society included an article by Zhu, Yuan-Yuan; Wu, Xue-Dan; Gu, Shuang-Xi; Pu, Lin. Synthetic Route of C7H9NO2. The article was titled 《Free Amino Acid Recognition: A Bisbinaphthyl-Based Fluorescent Probe with High Enantioselectivity》. The information in the text is summarized as follows:

A novel fluorescent probe based on a bisbinaphthyl structure was designed and synthesized. This compound in combination with Zn(II) has exhibited highly enantioselective fluorescence enhancement with 13 common free amino acids. For example, its enantiomeric fluorescent enhancement ratios (ef or ΔIL/ΔID) in the presence of the following amino acids are extremely high: 177 for valine, 199 for methionine, 186 for phenylalanine, 118 for leucine, and 89 for alanine. The observed high enantioselectivity and the extent of the substrate scope are unprecedented in the fluorescent recognition of free amino acids. This fluorescent probe can be applied to determine the enantiomeric composition of the structurally diverse chiral amino acids. NMR and mass spectroscopic studies provided clues to elucidate the observed high enantioselectivity. The experimental process involved the reaction of 2,6-Pyridinedimethanol(cas: 1195-59-1Synthetic Route of C7H9NO2)

2,6-Pyridinedimethanol(cas: 1195-59-1) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Synthetic Route of C7H9NO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Angewandte Chemie, International Edition included an article by Garreau, Marion; Le Vaillant, Franck; Waser, Jerome. Reference of 3-Bromopropan-1-ol. The article was titled 《C-Terminal bioconjugation of peptides through photoredox catalyzed decarboxylative alkynylation》. The information in the text is summarized as follows:

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. By the use of hypervalent iodine reagents, the introduction of a broad range of functional groups was successful. C-terminal selectivity was achieved by differentiation of the oxidation potentials of the carboxylic acids based on the use of fine-tuned organic dyes. The experimental process involved the reaction of 3-Bromopropan-1-ol(cas: 627-18-9Reference of 3-Bromopropan-1-ol)

3-Bromopropan-1-ol(cas: 627-18-9) was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and molten salt-polymers. Furthermore, it was used in the synthesis of chiral, quaternary prolines via cyclization of quaternary amino acids.Reference of 3-Bromopropan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,European Journal of Medicinal Chemistry included an article by Pisani, Leonardo; Iacobazzi, Rosa Maria; Catto, Marco; Rullo, Mariagrazia; Farina, Roberta; Denora, Nunzio; Cellamare, Saverio; Altomare, Cosimo Damiano. Formula: C3H7BrO. The article was titled 《Investigating alkyl nitrates as nitric oxide releasing precursors of multitarget acetylcholinesterase-monoamine oxidase B inhibitors》. The information in the text is summarized as follows:

Herein we envisaged the possibility of exploiting alkyl nitrates as precursors of alc.-bearing dual inhibitors targeting acetylcholinesterase (AChE) and monoamine oxidase B (MAO B), key enzymes in neurodegenerative syndromes such as Alzheimer’s disease (AD), through biotransformation unmasking an alc. function upon nitric oxide (NO) release. The cooperation to neuroprotection of low fluxes of NO and target enzymes’ inhibition by the alc. metabolites might return a multitargeting effect. The in vitro screening towards ChEs and MAOs of a collection of 21 primary alcs. disclosed a subset of dual inhibitors, among which three diverse chemotypes were selected to study the corresponding nitrates. Nitrate 14 proved to be a brain permeant, potent AChE-MAO B inhibitor by itself. Moreover, it protected human SH-SY5Y lines against rotenone and hydrogen peroxide with a poor inherent cytotoxicity and showed a slow conversion profile to its alc. metabolite 9d that still behaved as bimodal and neuroprotective mol. After reading the article, we found that the author used 3-Bromopropan-1-ol(cas: 627-18-9Formula: C3H7BrO)

3-Bromopropan-1-ol(cas: 627-18-9) was used in the synthesis of fluorescent halide-sensitive quinolinium dyes and molten salt-polymers. Furthermore, it was used in the synthesis of chiral, quaternary prolines via cyclization of quaternary amino acids.Formula: C3H7BrO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Tan, Qiuyuan; Wang, Xinqiao; Xiong, Yang; Zhao, Zimeng; Li, Lu; Tang, Pei; Zhang, Min published 《Chiral Amino Alcohol Accelerated and Stereocontrolled Allylboration of Iminoisatins: Highly Efficient Construction of Adjacent Quaternary Stereogenic Centers》.Angewandte Chemie, International Edition published the findings.Application of 126456-43-7 The information in the text is summarized as follows:

We have developed a highly efficient asym. allylboration of ketimines with nonchiral γ,γ-disubstituted allylboronic acids by using a chiral amino alc. as the directing group, which is otherwise challenging. The amino alc. not only serves as a cheap source of nitrogen and chirality, but also dramatically enhances the reactivity. The versatility of this method was demonstrated by its ability to access all four stereoisomers with adjacent quaternary carbon centers. A reaction model was proposed to explain the diastereoselectivity and the rate-accelerating effect. The experimental part of the paper was very detailed, including the reaction process of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7Application of 126456-43-7)

(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) 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.Application of 126456-43-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Park, Sun Jun; Kim, Eunjin; Yoo, Miyoun; Lee, Joo-Youn; Park, Chi Hoon; Hwang, Jong Yeon; Ha, Jae Du published 《Synthesis and biological evaluation of N9-cis-cyclobutylpurine derivatives for use as cyclin-dependent kinase (CDK) inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.Related Products of 27489-62-9 The information in the text is summarized as follows:

A novel 6-aminopurine scaffold bearing an N9-cis-cyclobutyl moiety was designed using structure-based mol. design based on two known CDK inhibitors, dinaciclib and Compound I. A series of novel 6-aminopurine compounds was prepared for structure-activity relationship (SAR) studies of CDK2 and CDK5 inhibitors. Among the compounds synthesized, compound II displayed potent CDK2 and CDK5 inhibitory activities with low nanomolar ranges (IC50 = 2.1 and 4.8 nM, resp.) and showed moderate cytotoxicity in HCT116 colon cancer and MCF7 breast cancer cell lines. Here, we report the synthesis and evaluation of novel 6-aminopurine derivatives and present mol. docking models of compound I with CDK2 and CDK5. The experimental process involved the reaction of trans-4-Aminocyclohexanol(cas: 27489-62-9Related Products of 27489-62-9)

trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Related Products of 27489-62-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2015,Wang, Zhaobin; Sheong, Fu Kit; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Sun, Jianwei published 《Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines》.Journal of the American Chemical Society published the findings.Electric Literature of C3H8ClNO The information in the text is summarized as follows:

The first catalytic asym. desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermol. reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combination of catalyst, nucleophile, protective group, and reaction conditions. The highly enantioenriched densely functionalized products are versatile precursors to other useful chiral mols. Mechanistic studies, including DFT calculations, revealed that only one catalyst mol. is involved in the key transition state, though both reactants can be activated. Also, the Curtin-Hammett principle dictates the reaction proceeds via amide nitrogen activation. The experimental part of the paper was very detailed, including the reaction process of Azetidin-3-ol hydrochloride(cas: 18621-18-6Electric Literature of C3H8ClNO)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Electric Literature of C3H8ClNO Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2013,Ishida, Naoki; Shimamoto, Yasuhiro; Yano, Takaaki; Murakami, Masahiro published 《1,5-Rhodium Shift in Rearrangement of N-Arenesulfonylazetidin-3-ols into Benzosultams》.Journal of the American Chemical Society published the findings.Quality Control of Azetidin-3-ol hydrochloride The information in the text is summarized as follows:

In the presence of [Rh(COD)(OH)]2 and the nonracemic bibenzodioxolediphosphine (R)-difluorphos, 1-arylsulfonyl-3-aryl-3-azetidinols such as I (R = Ph, 4-MeOC6H4, 4-F3CC6H4; Ts = 4-MeC6H4SO2) underwent enantioselective rearrangement to give fused thiazinediones such as II (R = Ph, 4-MeOC6H4, 4-F3CC6H4) in 90-95% yields and in 91:9-93:7 er. Stereoselective rearrangement of nonracemic amino acid-derived 1-arylsulfonyl-3-aryl-3-azetidinols such as III (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) in the presence of racemic 2,2′-bis{bis(3,5-xylyl)phosphino}-1,1′-binaphthyl yielded fused dihydrohydroxythiazinediones such as IV (R1 = Ph, 4-MeOC6H4, 4-F3CC6H4; R2 = Me, Me2CH, MeSCH2CH2; R3 = H, Me, MeO, F3C; R4 = H, Me) as single diastereomers and enantiomers in 97-99% yields. Rearrangement of I (R = Ph) with a perdeuterated tosyl group yielded a deuterated product monolabeled at the N-Me group; a mechanism for the rearrangement is proposed. The structure of IV (R1 = Ph; R2 = Me; R3 = Me; R4 = H) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Azetidin-3-ol hydrochloride(cas: 18621-18-6Quality Control of Azetidin-3-ol hydrochloride)

Azetidin-3-ol hydrochloride(cas:18621-18-6) is one of azetidine.Azetidines (azacyclobutanes) constitute a well-known class of heterocyclic compounds. Azetidine scaffold has been discovered in several natural products.Quality Control of Azetidin-3-ol hydrochloride Several pharmacologically important synthetic compounds also contain azetidine ring. Because of inherent ring strain, the synthesis of azetidines is a challenging endeavor.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application In Synthesis of 2,6-PyridinedimethanolIn 2020 ,《Thermally-Stable Imidazolium Dicationic Ionic Liquids with Pyridine Functional Groups》 was published in ACS Sustainable Chemistry & Engineering. The article was written by Clarke, Coby J.; Bui-Le, Liem; Hallett, Jason P.; Licence, Peter. The article contains the following contents:

Thermally-stable ionic liquids (ILs) have limited structural possibilities and lack coordinating anions or functional groups. Thermal stability effectively incurs a tunability penalty, limiting ionic liquid function to render them as simple heat-stable fluids. In this work, a series of new thermally-stable dicationic ionic liquids with pyridine functional groups, abbreviated [(C8ImC1)2Py][A]2, are presented and compared to nonfunctional geminal dicationic ILs. All ILs have been thermally characterized to understand their elevated temperature stabilities and the processes that lead to their decomposition Importantly, functional [(C8ImC1)2Py][A]2 with noncoordinating anions (i.e., [NTf2]-) have thermal stabilities comparable to those of geminal dicationic ILs, with the added advantage of a functional pyridine moiety. Dissolution of Zn[NTf2]2 in [(C8ImC1)2Py][NTf2]2 is demonstrated, and the resulting solutions are characterized to show their liquid properties, high thermal stabilities, and the coordination of the metal center to the functional group. This is the first example of a thermally-stable functional IL with the potential to reclaim the tunable, task-specific nature of ILs at elevated temperatures Importantly, these properties open new avenues for high-temperature applications of IL by extending their operational ranges; catalysis, metal remediation, and separation-based applications are potential key areas of improvement. A thermally-stable, functional ionic liquid is described that can extend the operating ranges of task-specific ionic liquids In addition to this study using 2,6-Pyridinedimethanol, there are many other studies that have used 2,6-Pyridinedimethanol(cas: 1195-59-1Application In Synthesis of 2,6-Pyridinedimethanol) was used in this study.

2,6-Pyridinedimethanol(cas: 1195-59-1) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Application In Synthesis of 2,6-Pyridinedimethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

HPLC of Formula: 126456-43-7In 2020 ,《CuII/TEMPO-Catalyzed Enantioselective C(sp3)-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation》 was published in Angewandte Chemie, International Edition. The article was written by Gao, Pei-Sen; Weng, Xin-Jun; Wang, Zhen-Hua; Zheng, Chao; Sun, Bing; Chen, Zhi-Hao; You, Shu-Li; Mei, Tian-Sheng. The article contains the following contents:

A novel strategy for asym. Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochem., affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported. The results came from multiple reactions, including the reaction of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7HPLC of Formula: 126456-43-7)

(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.HPLC of Formula: 126456-43-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts