Tag: 100-200

《Gold(I)/Gold(III) Catalysis that Merges Oxidative Addition and π-Alkene Activation》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Rigoulet, Mathilde; Thillaye du Boullay, Olivier; Amgoune, Abderrahmane; Bourissou, Didier. Application of 821-41-0 The article mentions the following:

Heteroarylation of alkenes with aryl iodides was efficiently achieved with a (MeDalphos)AuCl complex through AuI/AuIII catalysis. The possibility to combine oxidative addition of aryl iodides and π-activation of alkenes at gold is demonstrated for the first time. The reaction is robust and general (>30 examples including internal alkenes, 5-, 6-, and 7-membered rings). It is regioselective and leads exclusively to trans addition products. The (P,N) gold complex is most efficient with electron-rich aryl substrates, which are troublesome with alternative photoredox/oxidative approaches. In addition, it provides a very unusual switch in regioselectivity from 5-exo to 6-endo cyclization between the Z and E isomers of internal alkenols. After reading the article, we found that the author used 5-Hexen-1-ol(cas: 821-41-0Application of 821-41-0)

5-Hexen-1-ol(cas: 821-41-0) is a volatile organic compound. Further, it is used to prepare 6-bromo-hex-1-ene by reaction with phosphorus tribromide.Application of 821-41-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The author of 《Polyfunctional Bis-Lewis-Acid-/Bis-Triazolium Catalysts for Stereoselective 1,4-Additions of 2-Oxindoles to Maleimides》 were Schmid, Juliane; Junge, Thorsten; Lang, Johannes; Frey, Wolfgang; Peters, Rene. And the article was published in Angewandte Chemie, International Edition in 2019. Reference of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol The author mentioned the following in the article:

A novel type of polyfunctional catalyst, which contains Lewis acidic cobalt centers and triazolium moieties was developed. This catalyst type enabled highly enantio- and diastereoselective synthesis of substituted indoles I [R1 = H, Boc; R2 = Me, CH2C6H11, Bn, etc.; R3 = H, 5-Me, 5-Br, etc.] via direct 1,4-additions of 3-substituted oxindoles to maleimides with generation of two adjacent stereocenters. After use, the catalyst could be readily recycled by precipitation and used again with similar efficiency. Based on kinetic studies, a cooperative mode of action was very likely. Control experiments revealed the necessity of the triazolium rings for high stereoselectivity, which was explained by hydrogen-bond activation. 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: 126456-43-7Reference of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol)

(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Reference of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Journal of the American Chemical Society included an article by Kottisch, Veronika; O’Leary, Jacob; Michaudel, Quentin; Stache, Erin E.; Lambert, Tristan H.; Fors, Brett P.. COA of Formula: C6H12O. The article was titled 《Controlled Cationic Polymerization: Single-Component Initiation under Ambient Conditions》. The information in the text is summarized as follows:

Cationic polymerizations provide a valuable strategy for preparing macromols. with excellent control but are inherently sensitive to impurities and commonly require rigorous reagent purification, low temperatures, and strictly anhydrous reaction conditions. By using pentacarbomethoxycyclopentadiene (PCCP) as the single-component initiating organic acid, we found that a diverse library of vinyl ethers can be controllably polymerized under ambient conditions. Addnl., excellent chain-end fidelity is maintained even without rigorous monomer purification We hypothesize that a tight ion complex between the PCCP anion and the oxocarbenium ion chain end prevents chain-transfer events and enables a polymerization with living characteristics. Furthermore, terminating the polymerization with functional nucleophiles allows for chain-end functionalization in high yields. The experimental part of the paper was very detailed, including the reaction process of 5-Hexen-1-ol(cas: 821-41-0COA of Formula: C6H12O)

5-Hexen-1-ol(cas: 821-41-0) is a volatile organic compound. Further, it is used to prepare 6-bromo-hex-1-ene by reaction with phosphorus tribromide.COA of Formula: C6H12O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,European Journal of Medicinal Chemistry included an article by Hussein, Buthaina; Ikhmais, Balqis; Kadirvel, Manikandan; Magwaza, Rachael N.; Halbert, Gavin; Bryce, Richard A.; Stratford, Ian J.; Freeman, Sally. Quality Control of 3,5-Dihydroxybenzaldehyde. The article was titled 《Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinone oxidoreductase-2 (NQO2)》. The information in the text is summarized as follows:

N1-ribosyl-, N1-methyl-, N1-benzyl-dihydronicotinamide:quinone oxidoreductase 2 (NQO2) is associated with various processes involved in cancer initiation and progression probably via the production of ROS during quinone metabolism Thus, there is a need to develop inhibitors of NQO2 that are active in vitro and in vivo. As part of a strategy to achieve this, 4-aminoquinoline backbone is used as a starting point and synthesized I [R = Me], II [R1 = Ph, 4-imidazoyl, 2-nitrofuranyl, etc.], III novel analogs. The syntheses utilized p-anisidine with Meldrum’s acid and tri-Me orthoacetate or tri-Me orthobenzoate to give the 4-hydrazin-quinoline scaffold I [R = Me, Ph], which was derivatized with aldehydes R1CHO or acid chlorides R1C(O)Cl to give hydrazone II or hydrazide analogs III, resp. The hydrazones II were the most potent inhibitors of NQO2 in cell free systems, some with low nano-molar IC50 values. Structure-activity anal. highlighted the importance of a small substituent at the 2-position of the 4-aminoquinoline ring, to reduce steric hindrance and improve engagement of the scaffold within the NQO2 active site. Cytotoxicity and NQO2-inhibitory activity in vitro was evaluated using ovarian cancer SKOV-3 and TOV-112 cells (expressing high and low levels of NQO2, resp.). Generally, the hydrazones were more toxic than hydrazide analogs and further, toxicity is unrelated to cellular NQO2 activity. Pharmacol. inhibition of NQO2 in cells was measured using the toxicity of CB1954 as a surrogate end-point. Both the hydrazone II and hydrazide derivs III. are functionally active as inhibitors of NQO2 in the cells, but at different inhibitory potency levels. In particular, 4-((2-(6-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenol has the greatest potency of any compound yet evaluated (53 nM), which is 50-fold lower than its toxicity IC50. This compound and some of its analogs could serve as useful pharmacol. probes to determine the functional role of NQO2 in cancer development and response to therapy. The experimental process involved the reaction of 3,5-Dihydroxybenzaldehyde(cas: 26153-38-8Quality Control of 3,5-Dihydroxybenzaldehyde)

3,5-Dihydroxybenzaldehyde(cas: 26153-38-8) is used as a building block in the synthesis of more complex structures. It is also used in the synthesis of terbutaline, which is an important bronchodilator.Quality Control of 3,5-Dihydroxybenzaldehyde

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Bioorganic & Medicinal Chemistry Letters included an article by Thanh, Nguyen Dinh; Hai, Do Son; Ha, Nguyen Thi Thu; Tung, Do Tien; Le, Cao Thi; Van, Hoang Thi Kim; Toan, Vu Ngoc; Toan, Duong Ngoc; Dang, Le Hai. Synthetic Route of C7H6O2. The article was titled 《Synthesis, biological evaluation and molecular docking study of 1,2,3-1H-triazoles having 4H-pyrano[2,3-d]pyrimidine as potential Mycobacterium tuberculosis protein tyrosine phosphatase B inhibitors》. The information in the text is summarized as follows:

Some heterocycles, namely 2-amino-4H-pyran-3-carbonitriles, were synthesized in a three-component reaction from substituted benzaldehydes, malononitrile, and Et acetoacetate. These heterocycles have been converted subsequently into 4H-pyrano[2,3-d]pyrimidine ring by ring-closing reaction with acetic anhydride in the presence of the concentrated sulfuric acid as catalyst. The successive alkylation reaction of lactam N-H bond on pyrimidine-4-one ring was carried out using propargylic bromide in dry acetone in the presence of anhydrous potassium carbonate. The click chem. of 3-propargyl-4H-pyrano[2,3-d]pyrimidine compounds has been accomplished by reaction with tetra-O-acetyl-α-D-glucopyranosyl azide using the metal-organic framework Cu@MOF-5 as a catalyst in absolute ethanol. All the synthesized 1H-1,2,3-triazoles were screened for their in vitro Mycobacterium tuberculosis protein tyrosine phosphatase B (MtbPtpB) inhibition. Kinetic studies of the most active compounds I (R = 3,5-diOMe-4-OH, 3-OH-4-OEt, 3-OMe-4-OH-5-NO2) showed their competitive inhibition toward the MtbPtpB enzyme. The detailed structure-activity relationship (SAR) in vitro and in silico studies suggested that the interaction of Arg63 amino acids with anion type of para-hydroxyl group via a salt bridge of iminium cation was essential for strong inhibitory activity against MtbPtpB.3-Hydroxybenzaldehyde(cas: 100-83-4Synthetic Route of C7H6O2) was used in this study.

3-Hydroxybenzaldehyde(cas: 100-83-4) can be used as a reactant along with ethyl acetoacetate and thiourea in the synthesis of corresponding dihydropyrimidine-2-thione (monastrol), using Yb(OTf)3 as a catalyst by Biginelli cyclocondensation reaction.Synthetic Route of C7H6O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2018,Engelsma, Sander B.; van den Ende, Thomas C.; Overkleeft, Hermen S.; van der Marel, Gijsbert A.; Filippov, Dmitri V. published 《Reaction Rates of Various N-Acylenamines in the Inverse-Electron-Demand Diels-Alder Reaction》.European Journal of Organic Chemistry published the findings.Related Products of 18621-18-6 The information in the text is summarized as follows:

In light of the bioorthogonal inverse-electron-demand Diels-Alder strategy, an extended investigation into the effects of ring strain and electron inductive effects on the reactivity of the N-acylenamine core towards tetrazine has been carried out. Through a comparative study between N-acylazetines, N-vinylcarbamates and an N-vinylamide it was shown that ring strain has a more significant effect on reaction rate than electron donation. A significantly improved synthetic route is reported for the preparation of an N-acylazetine biorthogonal tag reported previously. The results came from multiple reactions, including the reaction of Azetidin-3-ol hydrochloride(cas: 18621-18-6Related Products of 18621-18-6)

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.Related Products of 18621-18-6 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 2017,Yefidoff-Freedman, Revital; Fan, Jing; Yan, Lu; Zhang, Qingwen; dos Santos, Guillermo Rodrigo Reis; Rana, Sandeep; Contreras, Jacob I.; Sahoo, Rupam; Wan, Debin; Young, Jun; Dias Teixeira, Karina Luiza; Morisseau, Christophe; Halperin, Jose; Hammock, Bruce; Natarajan, Amarnath; Wang, Peimin; Chorev, Michael; Aktas, Bertal H. published 《Development of 1-((1,4-trans)-4-Aryloxycyclohexyl)-3-arylurea Activators of Heme-Regulated Inhibitor as Selective Activators of the Eukaryotic Initiation Factor 2 Alpha (eIF2α) Phosphorylation Arm of the Integrated Endoplasmic Reticulum Stress Response》.Journal of Medicinal Chemistry published the findings.Application of 27489-62-9 The information in the text is summarized as follows:

Heme-regulated inhibitor (HRI), an eukaryotic translation initiation factor 2 alpha (eIF2α) kinase, plays critical roles in cell proliferation, differentiation, adaptation to stress, and Hb disorders. HRI phosphorylates eIF2α that couples cellular signals including the endoplasmic reticulum (ER) stress to translation. The authors previously identified 1,3-diarylureas and 1-((1,4-trans)-4-aryloxycyclohexyl)-3-arylureas (cHAUs) as specific activators of HRI that trigger the eIF2α phosphorylation arm of ER-stress response as mol. probes for studying HRI biol. and its potential as a druggable target. To develop drug-like cHAUs needed for in vivo studies the authors undertook bioassay guided structure-activity relationship studies and tested them in the surrogate eIF2α phosphorylation and cell proliferation assays. The authors further evaluated some of these cHAUs in endogenous eIF2α phosphorylation and expression of the transcription factor CHOP protein and mRNA demonstrating significantly improved solubility and/or potencies. These cHAUs are excellent candidates for lead optimization for development of investigational new drugs that potently and specifically activate HRI. In the part of experimental materials, we found many familiar compounds, such as trans-4-Aminocyclohexanol(cas: 27489-62-9Application of 27489-62-9)

trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Application of 27489-62-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Gunia-Krzyzak, Agnieszka; Zelaszczyk, Dorota; Rapacz, Anna; Zeslawska, Ewa; Waszkielewicz, Anna M.; Panczyk, Katarzyna; Sloczynska, Karolina; Pekala, Elzbieta; Nitek, Wojciech; Filipek, Barbara; Marona, Henryk published 《Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH3 or 2-CH3》.Bioorganic & Medicinal Chemistry published the findings.Quality Control of trans-4-Aminocyclohexanol The information in the text is summarized as follows:

A series of twenty two (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in Ph ring with 4-Cl, 4-CH3 or 2-CH3 was designed, synthesized and evaluated for anticonvulsant activity in rodent models of seizures: maximal electroshock (MES) test, s.c. pentylenetetrazole (scPTZ) test, and 6-Hz test. There were identified three most active compounds: S-(2E)-N-(1-hydroxypropan-2-yl)-3-(2-methylphenyl)prop-2-enamide (5) (ED50 MES = 42.56, ED50 scPTZ = 58.38, ED50 6-Hz 44 mA = 42.27 mg/kg tested in mice after i.p. (i.p.) administration); R,S-(2E)-3-(4-chlorophenyl)-N-(1-hydroxybutan-2-yl)prop-2-enamide (6) (ED50 MES = 53.76, ED50 scPTZ = 90.31, ED50 6-Hz 44 mA = 92.86 mg/kg mice, i.p.); and R,S-(2E)-3-(4-chlorophenyl)-N-(2-hydroxypropyl)prop-2-enamide (11) (ED50 MES = 55.58, ED50 scPTZ = 102.15, ED50 6-Hz 44 mA = 51.27 mg/kg mice, i.p.). Their structures and configurations were confirmed by crystal X-ray diffraction method. The structure-activity studies among the tested series showed that chlorine atom in position para or Me group in position ortho of Ph ring were beneficial for anticonvulsant activity. Me group in position para of Ph ring decreased anticonvulsant activity in reported series of cinnamamide derivatives The experimental process involved the reaction of trans-4-Aminocyclohexanol(cas: 27489-62-9Quality Control of trans-4-Aminocyclohexanol)

trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Quality Control of trans-4-Aminocyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2007,Provins, Laurent; Christophe, Bernard; Danhaive, Pierre; Dulieu, Jacques; Gillard, Michel; Quere, Luc; Stebbins, Karin published 《Dual M3 antagonists-PDE4 inhibitors. Part 2: Synthesis and SAR of 3-substituted azetidinyl derivatives》.Bioorganic & Medicinal Chemistry Letters published the findings.SDS of cas: 18621-18-6 The information in the text is summarized as follows:

Introduction of 3-substituted azetidinyl substituents onto the 4,6-diaminopyrimidine scaffold allowed the improvement of PDE4 inhibiting activities. Preliminary in vivo activity in pulmonary inflammation models is reported.Azetidin-3-ol hydrochloride(cas: 18621-18-6SDS of cas: 18621-18-6) was used in this study.

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.SDS of cas: 18621-18-6 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

《Molecular structure of cefuroxime axetil complexes with α-, β-, γ-, and 2-hydroxypropyl-β-cyclodextrins: molecular simulations and Raman spectroscopic and imaging studies》 was published in International Journal of Molecular Sciences in 2021. These research results belong to Gieroba, Barbara; Kalisz, Grzegorz; Sroka-Bartnicka, Anna; Plazinska, Anita; Plazinski, Wojciech; Starek, Malgorzata; Dabrowska, Monika. HPLC of Formula: 54-17-1 The article mentions the following:

The formation of cefuroxime axetil + cyclodextrin (CA + CD) complexes increases the aqueous solubility of CA, improves its physico-chem. properties, and facilitates a biomembrane-mediated drug delivery process. In CD-based tablet formulations, it is crucial to investigate the mol. details of complexes in final pharmaceutical preparation In this study, Raman spectroscopy and mapping were applied for the detection and identification of chem. groups involved in α-, β-, γ-, and 2-hydroxypropyl-β-CD (2-HP- β-CD) + CA complexation process. The exptl. studies have been complemented by mol. dynamics-based investigations, providing addnl. mol. details of CA + CD interactions. It has been demonstrated that CA forms the guest-host type inclusion complexes with all studied CDs; however, the nature of the interactions is slightly different. It seems that both α- and β-CD interact with furanyl and methoxy moieties of CA, γ-CD forms a more diverse pattern of interactions with CA, which are not observed in other CDs, whereas 2HP-β-CD binds CA with the contribution of hydrogen bonding. Apart from supporting this interpretation of the exptl. data, mol. dynamics simulations allowed for ordering the CA + CD binding affinities. The obtained results proved that the mol. details of the host-guest complexation can be successfully predicted from the combination of Raman spectroscopy and mol. modeling. The results came from multiple reactions, including the reaction of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(cas: 54-17-1HPLC of Formula: 54-17-1)

rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(cas: 54-17-1) is oxidized in various tissues under either aerobic or anaerobic conditions through glycolysis; the oxidation reaction produces carbon dioxide, water, and ATP.HPLC of Formula: 54-17-1

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts