Month: October 2022

《Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation》 was written by Wang, Johnny Z.; Sakai, Holt A.; MacMillan, David W. C.. Category: alcohols-buliding-blocks And the article was included in Angewandte Chemie, International Edition on August 26 ,2022. The article conveys some information:

Herein, an operationally convenient, N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition of alc.-derived alkyl radicals to electron-deficient alkenes under mild photocatalytic conditions was described. The fragment coupling accommodated a broad range of primary, secondary, and tertiary alc. partners, as well as structurally varied Michael acceptors containing traditionally reactive sites, such as electrophilic or oxidizable moieties. The late-stage diversification of densely functionalized mol. architectures, including drugs and biomols. was demonstrated, and this protocol with metallaphotoredox cross-coupling for step-economic access to sp3-rich complexity was telescoped. In the experiment, the researchers used ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6Category: alcohols-buliding-blocks)

((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6) is a useful reactant for examining the effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-​II (CA-​II)​.Category: alcohols-buliding-blocks And it is used as chiral auxiliaries in Michael and Aldol addition reactions.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Synthesis, in vitro evaluation, and molecular docking studies of benzofuran based hydrazone a new inhibitors of urease》 was written by Abdullah Al-Mohammadi, Jana; Taha, Muhammad; Rahim, Fazal; Hussain, Rafaqat; aldossary, Hanan; Khalid Farooq, Rai; Wadood, Abdul; Nawaz, Muhammad; Salahuddin, Mohammed; Mohammed Khan, Khalid; Uddin, Nizam. Product Details of 26153-38-8This research focused onurease inhibitor benzofuran hydrazone mol docking. The article conveys some information:

This work has described the synthesis of novel class (1-25) of benzofuran based hydrazone. The hybrid scaffolds (1-25) of benzofuran based hydrazone were evaluated in vitro, for their urease inhibition. All the newly synthesized analogs (1-25) were found to illustrate moderate to good urease inhibitory profile ranging from 0.20 ± 0.01 to 36.20 ± 0.70 μM. Among the series, compounds 22 (IC50 = 0.20 ± 0.01 μM), 5 (IC50 = 0.90 ± 0.01 μM), 23 (IC50 = 1.10 ± 0.01 μM) and 25 (IC50 = 1.60 ± 0.01 μM) were found to be the many folds more potent than thiourea as standard inhibitor (IC50 = 21.86 ± 0.40 μM). The elevated inhibitory profile of these analogs might be due to presence of dihydroxy and flouro groups at different position of Ph ring B attached to hydrazone skeleton. These dihydroxy and fluoro groups bearing compounds have shown many folds better inhibitory profile through involvement of oxygen of dihydroxy groups in hydrogen bonding with active site of enzymes. Various types of spectroscopic techniques such as 1H-, 13C- NMR and HREI-MS spectroscopy were used to confirm the structure of all the newly developed compounds To find SAR, mol. docking studies were performed to understand, the binding mode of potent inhibitors with active site of enzymes and results supported the exptl. data. The results came from multiple reactions, including the reaction of 3,5-Dihydroxybenzaldehyde(cas: 26153-38-8Product Details of 26153-38-8)

3,5-Dihydroxybenzaldehyde(cas: 26153-38-8) is a building block. It has been used in the synthesis of 2,4-dimethylbenzoylhydrazones with antileishmanial and antioxidant activities.Product Details of 26153-38-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 1994,Bulletin de la Societe Chimique de France included an article by Berkous, Rabia; Dupas, Georges; Bourguignon, Jean; Queguiner, Guy. Recommanded Product: (3-Chlorophenyl)(phenyl)methanol. The article was titled 《Behavior and extension of the scope of NADH models to the reduction of non-activated ketones by a stable indolo NADH model compound in the presence of Lewis acids》. The information in the text is summarized as follows:

The reduction of non-activated ketones, e.g., acetophenone, by a very stable NADH model in the presence of Lewis acids (AlX3, Et2AlCl) is reported. During the reaction, a side equilibrated aldol condensation occurs. Due to the reversibility of this reaction, the overall yield in alc. is not notably diminished. The scope of NADH models has been extended for the first time to non-activated ketones, such as dialkyl, aryl alkyl and diaryl ketones. In the experimental materials used by the author, we found (3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3Recommanded Product: (3-Chlorophenyl)(phenyl)methanol)

(3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains. The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.Recommanded Product: (3-Chlorophenyl)(phenyl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The author of 《Synthesis, antibacterial and antifungal activities of bifonazole derivatives》 were El Hage, Salome; Lajoie, Barbora; Feuillolay, Catherine; Roques, Christine; Baziard, Genevieve. And the article was published in Archiv der Pharmazie (Weinheim, Germany) in 2011. Product Details of 63012-03-3 The author mentioned the following in the article:

Two series of chlorinated benzhydryl imidazole and triazole derivatives were synthesized and tested in vitro against representative strains of potent pathogenic bacteria (Staphylococcus aureus CIP 4.83, Enterococcus hirae CIP 5855, Pseudomonas aeruginosa CIP 82118, Escherichia coli CIP 53126) and fungi (Aspergillus niger IP 1431.83, Candida albicans IP 48.72, Candida krusei IP 208.52, Trichophyton rubrum IP 1657.86). Most of these compounds were devoid of any antimicrobial activity, but several of them inhibited T. rubrum with MIC values in the range 0.125-32 μg/mL, similar or superior to those of bifonazole and clotrimazole, used as standard controls. The replacement of the imidazole ring by a triazole moiety in these compounds led to derivatives with less antifungal activity. A preliminary SAR was undertaken on the effect of the number and the position of chlorine atoms on the distribution of neg. charge on the surface of some compounds on antifungal activity. In addition to this study using (3-Chlorophenyl)(phenyl)methanol, there are many other studies that have used (3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3Product Details of 63012-03-3) was used in this study.

(3-Chlorophenyl)(phenyl)methanol(cas: 63012-03-3) belongs to hydroxy-containing compounds. Hydroxy groups participate in the dehydration reactions that link simple biological molecules into long chains.Product Details of 63012-03-3 The joining of a fatty acid to glycerol to form a triacylglycerol removes the −OH from the carboxy end of the fatty acid.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Walker, Shawn D.; Borths, Christopher J.; DiVirgilio, Evan; Huang, Liang; Liu, Pingli; Morrison, Henry; Sugi, Kiyoshi; Tanaka, Masahide; Woo, Jacqueline C. S.; Faul, Margaret M. published an article in Organic Process Research & Development. The title of the article was 《Development of a Scalable Synthesis of a GPR40 Receptor Agonist》.Recommanded Product: (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid The author mentioned the following in the article:

Early process development and salt selection for AMG 837, a novel GPR40 receptor agonist, is described. The synthetic route to AMG 837 involved the convergent synthesis and coupling of two key fragments, (S)-3-(4-hydroxyphenyl)hex-4-ynoic acid (I) and 3-(bromomethyl)-4′-(trifluoromethyl)biphenyl (II). The chiral β-alkynyl acid I was prepared in 35% overall yield via classical resolution of the corresponding racemic acid (±)-I. An efficient and scalable synthesis of (±)-I was achieved via a telescoped sequence of reactions including the conjugate alkynylation of an in situ protected Meldrum’s acid derived acceptor. The biaryl bromide II was prepared in 86% yield via a 2-step Suzuki-Miyaura coupling-bromination sequence. Chemoselective phenol alkylation mediated by tetrabutylphosphonium hydroxide allowed direct coupling of I and II to afford AMG 837. Due to the poor physiochem. stability of the free acid form of the drug substance, a sodium salt form was selected for early development, and a more stable, crystalline hemicalcium salt dihydrate form was subsequently developed. Overall, the original 12-step synthesis of AMG 837 was replaced by a robust 9-step route affording the target in 25% yield. The experimental part of the paper was very detailed, including the reaction process of (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid(cas: 865233-35-8Recommanded Product: (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid)

(S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid(cas: 865233-35-8) belongs to alkynes. The addition of nonpolar E−H bonds across C≡C is general for silanes, boranes, and related hydrides.Recommanded Product: (S)-3-(4-Hydroxyphenyl)hex-4-ynoic acid The hydroboration of alkynes gives vinylic boranes which oxidize to the corresponding aldehyde or ketone. In the thiol-yne reaction the substrate is a thiol.

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

In 2016,Wysoczanska, Kamila; Macedo, Eugenia A. published 《Influence of the Molecular Weight of PEG on the Polymer/Salt Phase Diagrams of Aqueous Two-Phase Systems》.Journal of Chemical & Engineering Data published the findings.Recommanded Product: Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate The information in the text is summarized as follows:

Binodal data for systems composed by polyethylene glycol (PEG) (4000, 6000, or 8000) and salt (potassium citrate, potassium sodium tartrate) were obtained using the cloud point method, at T = 298.15 K. Merchuk equation was applied for the fitting of binodal curves. Tie-lines for systems of PEG (4000, 6000)-potassium citrate and PEG (4000, 6000, 8000)-potassium sodium tartrate were determined by elec. conductivity and lyophilization, and correlated using Othmer-Tobias and Bancroft equations, to verify the reliability of the measured tie-lines. Data were compared with that of previous studies reported in the literature, giving an indication of which system is more efficient in terms of separation, taking into account possible combinations of salt’s cations and PEGs of different mol. weight chosen for ATPS. In the experiment, the researchers used many compounds, for example, Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate(cas: 6381-59-5Recommanded Product: Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate)

Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate(cas: 6381-59-5) is a ferroelectric crystal with a high piezoelectric effect and electromechanical coupling coefficient. Recommanded Product: Potassium sodium (2R,3R)-2,3-dihydroxysuccinate tetrahydrate As a Biuret reagent, it is used to measure the protein concentration. Furthermore, it is used as laxative and is also used in food industry.

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 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 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