Month: October 2022

Reference of trans-4-AminocyclohexanolIn 2017 ,《Synthesis of 4-Heteroaryl-Quinazoline Derivatives as Potential Anti-breast Cancer Agents》 appeared in Journal of Heterocyclic Chemistry. The author of the article were Kassab, A. E.; Gedawy, E. M.; El-Nassan, H. B.. The article conveys some information:

The 4-heteroaryl or heteroalkyl-quinazoline derivatives e.g., I were prepared as dual epidermal growth factor receptor (EGFR) and vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors. These compounds were tested for their dual enzyme inhibition as well as their cytotoxic activity on MCF7 cell line. The results indicated that almost all the compounds showed moderate dual inhibition of both enzymes. The compound methyl1-(6,7-dimethoxyquinazolin-4-yl)piperidine-4-carboxylate showed the highest inhibitory activity against both enzymes with IC50 97.6 and 64.0 μM against EGFR and VEGFR-2 kinases, resp. Most of the test compounds showed potent to moderate antitumor activity on MCF7 cell line. Some of the compounds showed potent cytotoxic activity with IC50 values between 10 and 17 M. The results came from multiple reactions, including the reaction of trans-4-Aminocyclohexanol(cas: 27489-62-9Reference of trans-4-Aminocyclohexanol)

trans-4-Aminocyclohexanol(cas: 27489-62-9) 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 trans-4-Aminocyclohexanol

Referemce:
Alcohol – Wikipedia,
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Formula: C3H9NO2In 2020 ,《PH-responsive artesunate polymer prodrugs with enhanced ablation effect on rodent xenograft colon cancer》 was published in International Journal of Nanomedicine. The article was written by Hao, Dan-Li; Xie, Ran; De, Ge-Jing; Yi, Hong; Zang, Chen; Yang, Mi-Yi; Liu, Li; Ma, Hai; Cai, Wei-Yan; Zhao, Qing-He; Sui, Feng; Chen, Yan-Jun. The article contains the following contents:

Purpose: In this study, pH-sensitive poly(2-ethyl-2-oxazoline)-poly(lactic acid)-poly(β-amino ester) (PEOz-PLA-PBAE) triblock copolymers were synthesized and were conjugated with an antimalaria drug artesunate (ART), for inhibition of a colon cancer xenograft model. The as-prepared polymer prodrugs are tended to self-assemble into polymeric micelles in aqueous milieu, with PEOz segment as hydrophilic shell and PLA-PBAE segment as hydrophobic core. The pH sensitivity of the as-prepared copolymers was confirmed by acid-base titration with pKb values around 6.5. The drug-conjugated polymer micelles showed high stability for at least 96 h in PBS and 37°C, resp. The as-preparation copolymer prodrugs showed high drug loading content, with 9.57% ±1.24% of drug loading for PEOz-PLA-PBAE-ART4. The conjugated ART could be released in a sustained and pH-dependent manner, with 92% of released drug at pH 6.0 and 57% of drug released at pH 7.4, resp. In addition, in vitro experiments showed higher inhibitory effect of the prodrugs on rodent CT-26 cells than that of free ART. Animal studies also demonstrated the enhanced inhibitory efficacy of PEOz-PLA-PBAE-ART2 micelles on the growth of rodent xenograft tumor. The pH-responsive artesunate polymer prodrugs are promising candidates for colon cancer adjuvant therapy. The results came from multiple reactions, including the reaction of 2-Aminopropane-1,3-diol(cas: 534-03-2Formula: C3H9NO2)

2-Aminopropane-1,3-diol(cas: 534-03-2) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Formula: C3H9NO2

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Alcohol – Wikipedia,
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Formula: C7H6O2In 2021 ,《RP-HPLC analysis of phenolic lignin monomers with DAD and coulometric array detection》 was published in Journal of Chromatographic Science. The article was written by Fischer, Klaus; Hoeffler, Susanne. The article contains the following contents:

An high performance liquid chromatog. (HPLC) method, applying diode array (DAD) and coulometric array detection simultaneously, was developed to determine monomeric phenolic compounds in lignin hydrolyzates. To allow for addnl. mass spectrometric detection, a formic acid gradient was designed as an alternative to the non-volatile phosphate buffer gradient. Within a total run time of 28 min, 10 out of 14 analytes were baseline separated by the formic acid gradient, and 8 compounds were completely resolved by the phosphate gradient. The dependence of the coulometric detection on cell potential, potential step width, eluent pH and eluent composition was comprehensively tested. Detection limits ≤20μg/L were achieved by DAD detection for nine analytes and by coulometric array detection for all analytes, demonstrating the superior sensitivity of electrochem. detection. DAD offered better linearity and reproducibility. Inter-day precision of peak heights spanned from 0.26 to 2.00% (formic acid gradient) and from 0.75 to 2.85% (phosphate buffer gradient) operating the DAD detector, but it exceeded 10% for several compounds applying the coulometric array detector. The simultaneous operation of both detectors offered an enhanced certainty of substance identification. The appropriateness of the method was confirmed by the anal. of various hydrolyzates of lignin-containing materials. The results came from multiple reactions, including the reaction of 3-Hydroxybenzaldehyde(cas: 100-83-4Formula: C7H6O2)

3-Hydroxybenzaldehyde(cas: 100-83-4) is used as an ionophore, during the development of an highly selective and sensitive PVC membrane sensor, which can be used as a Tb3+ ion selective electrode.Formula: C7H6O2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of C6H7NOIn 2020 ,《Ruthenium Catalyzed Divergent Alkylation and Olefination of Methyl 1,3,5-Triazines with Alcohols》 was published in European Journal of Organic Chemistry. The article was written by Su, Chengwu; Zeng, Ming; Zhang, Chen; Cui, Dong-Mei. The article contains the following contents:

An efficient ruthenium-catalyzed divergent alkylation and olefination of Me 1,3,5-triazines with alcs. have been developed. The selectivity can be rationally tuned by the judicious choice of ruthenium catalyst, wherein Ru(PPh3)3Cl2 delivers alkylated 1,3,5-triazines and RuCl3 gives olefinated 1,3,5-triazines in up to 98% yield. Following this simple, facile, and high atom economical protocol, a broad range of products was prepared in moderate to good yields and tolerated heterocyclic or benzylic alcs. containing functionalities. The overall transformation operates through dehydrogenation of primary alcs. under the reaction conditions to provide the corresponding aldehydes, which further undergo condensation with Me 1,3,5-triazines. The experimental part of the paper was very detailed, including the reaction process of 3-Pyridinemethanol(cas: 100-55-0Synthetic Route of C6H7NO)

3-Pyridinemethanol(cas: 100-55-0) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Synthetic Route of C6H7NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Safety of 3-Aminopropan-1-olIn 2020 ,《Tunable Structural Color Patterns Based on the Visible-Light-Responsive Dynamic Diselenide Metathesis》 was published in Advanced Materials (Weinheim, Germany). The article was written by Liu, Cheng; Fan, Zhiyuan; Tan, Yizheng; Fan, Fuqiang; Xu, Huaping. The article contains the following contents:

Structural color materials with reversible stimuli-responsiveness to external environment have been widely used in sensors, encryption, display, and other fields. Compared with other stimuli, visible light is highly controllable both temporally and spatially with less damage to materials, which is more suitable for structural color patterning. Herein, a new diselenide-containing shape memory material is prepared and used for creating patterns via visible light stimulus. In this system, the structural color originates from birefringence of stretched materials, whose shapes can be fixed while maintaining the mech. stress. The fixed stress can be released by diselenide metathesis under visible light irradiation By regulating the wavelength or irradiation time with a com. projector, the pattern with tunable structural colors is realized and the structural color pattern can be erased and rewritten arbitrarily. During the patterning process, the optical signal is first stored as mech. signal and then transformed back to optical signal. It is a new method for preparing visible-light-responsive structural color material and has great potential in display devices, anticounterfeiting labels, and data storage. In the experimental materials used by the author, we found 3-Aminopropan-1-ol(cas: 156-87-6Safety of 3-Aminopropan-1-ol)

3-Aminopropan-1-ol(cas: 156-87-6) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Safety of 3-Aminopropan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Palladium-Catalyzed Barluenga-Valdes Type Cross-Coupling Reaction: Alkenylation of 7-Azaindoles》 was written by Raina, Gaurav; Kannaboina, Prakash; Ahmed, Qazi Naveed; Mondal, Krishanu; Das, Parthasarathi. Name: Oxetan-3-olThis research focused onvinyl azaindole preparation chemoselective; sulfonylhydrazone azaindole Barluenga Valdes cross coupling alkenylation palladium catalyst. The article conveys some information:

An efficient coupling method between sulfonylhydrazones ArC(CH3)=NNHTs (Ar = 3-nitrophenyl, pyridin-4-yl, naphthalen-2-yl, etc.) and 7-azaindoles I (R1 = H, 5-Br; R2 = H, I; R3 = Me, Bn, 4-methoxyphenyl) using Pd(OAc)2 as catalyst and dppf as ligand providing flexible and convergent access to different vinyl 7-azaindoles II and III is achieved. A wide variety of olefins II were obtained up to 86% yields via the coupling of numerous electronically distinct hydrazones with different 7-azaindoles I under the present catalytic conditions. The protocol was further extended to other heteroarenes such as indoles, quinolines, isoquinolines, and pyridine. The imperative feature of these protocols is its ease at the gram scale and their potential to get transformed into different valuable constructs. The experimental part of the paper was very detailed, including the reaction process of Oxetan-3-ol(cas: 7748-36-9Name: Oxetan-3-ol)

Oxetan-3-ol(cas: 7748-36-9) is used as a reagent in the synthesis of 5-fluoro-4,6-dialkoxypyrimidine GPR119 agonists. It is also used as a reagent in the synthesis of cyclic sulfone hydroxyethylamines as potent and selective β-site APP-cleaving enzyme 1 (BACE1) inhibitors.Name: Oxetan-3-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Zanthosides A-D: four aromatic glucosides from the leaves of Zanthoxylum ailanthoides》 was written by Teshima, Serika; Yamashita-Higuchi, Yukiko; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu. Application In Synthesis of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol And the article was included in Chemical & Pharmaceutical Bulletin on August 31 ,2020. The article conveys some information:

From the leaves of Zanthoxylum ailanthoides, four new phenolic glucosides, termed zanthosides A-D (1-4), were isolated. Their structures were elucidated by means of spectroscopic evidence. Zanthoside A was enzymically hydrolyzed and thus the aglycon obtained was found to be (1′S,2′R)-(-)-trans-decursidinol, isolated from Angelica decursiva. In addition to this study using rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol, there are many other studies that have used rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol(cas: 54-17-1Application In Synthesis of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol) was used in this study.

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.Application In Synthesis of rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application In Synthesis of 3,3,3-Trifluoropropan-1-olOn March 12, 2020, Pettus, Liping H.; Bourbeau, Matthew P.; Bradley, Jodi; Bartberger, Michael D.; Chen, Kui; Hickman, Dean; Johnson, Michael; Liu, Qingyian; Manning, James R.; Nanez, Adrian; Siegmund, Aaron C.; Wen, Paul H.; Whittington, Douglas A.; Allen, Jennifer R.; Wood, Stephen published an article in Journal of Medicinal Chemistry. The article was 《Discovery of AM-6494: A Potent and Orally Efficacious β-Site Amyloid Precursor Protein Cleaving Enzyme 1 (BACE1) Inhibitor with in Vivo Selectivity over BACE2》. The article mentions the following:

β-Site amyloid precursor protein cleaving enzyme 1 (BACE1) is an aspartyl protease that plays a key role in the production of amyloid β (Aβ) in the brain and has been extensively pursued as a target for the treatment of Alzheimer’s disease (AD). BACE2, an aspartyl protease that is structurally related to BACE1, has been recently reported to be involved in melanosome maturation and pigmentation. Herein, we describe the development of a series of cyclopropylthiazines as potent and orally efficacious BACE1 inhibitors. Lead optimization led to the identification of 20, a mol. with biochem. IC50 BACE2/BACE1 ratio of 47. Administration of 20 resulted in no skin/fur color change in a 13-day mouse hypopigmentation study and demonstrated robust and sustained reduction of CSF and brain Aβ40 levels in rat and monkey pharmacodynamic models. On the basis of a compelling data package, 20 (AM-6494) was advanced to preclin. development. The experimental process involved the reaction of 3,3,3-Trifluoropropan-1-ol(cas: 2240-88-2Application In Synthesis of 3,3,3-Trifluoropropan-1-ol)

3,3,3-Trifluoropropan-1-ol(cas: 2240-88-2) is a important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.Application In Synthesis of 3,3,3-Trifluoropropan-1-ol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

COA of Formula: C13H19Br2ClN2OOn September 30, 2022 ,《Facile approaches for determination of Bromhexine Hydrochloride and its active metabolite Ambroxol Hydrochloride using Eosin Y》 was published in Annales Pharmaceutiques Francaises. The article was written by El-Sayed, A.; Elmansi, H.; Shalan, S.; Eid, M.. The article contains the following contents:

New validated Spectroscopic methods were developed to assay Bromhexine Hydrochloride and its active metabolite Ambroxol Hydrochloride sep. in pure form and pharmaceutical formulations. The spectrophotometric assay (method I) shows complex formation between each of the drugs and Eosin Y at 540 nm at pH 3.6 and 3.4 mL of 4 x 10-4M Eosin for Bromhexine and Ambroxol. The Spectrofluorimetric assay (method II) depends on quenching eosin native fluorescence by the studied drugs, which measured at 540 nm after excitation at 302 nm. The spectrophotometric absorbance-concentration plot is rectilinear over the ranges (1.0-5.0) and (1.0-10.0) μg/mL for bromhexine and ambroxol with LOD of 0.31 and 0.14μg/mL and LOQ of 0.94 and 0.42μg/mL for the two drugs resp. The fluorometric-concentration plot is linear along the range (1.0-5.0) μg/mL and (1-10) μg/mL for the two drugs resp. with LOD of 0.13μg/mL and 0.22μg/mL and LOQ of 0.4μg/mL and 0.65μg/mL for the two drugs, resp. Developed assays have been validated in agreement with ICH recommendations and they were used in the anal. of com. drug formulations containing the two mucolytic drugs and the results were matching with those obtained by the comparison method.De nouvelles methodes spectroscopiques validees ont etedeveloppes pour doser le chlorhydrate de bromhexine et son metabolite actif, le chlorhydrate d’Ambroxol, sous forme pure et dans des formulations pharmaceutiques. Le dosage spectrophotometrique (methode I) montre la formation d’un complexe entre chacun des medicaments et l’eosine Y a540 nm a pH 3,6 et 3,4 mL d’eosine 4 x 10-4M pour la bromhexine et l’ambroxol. Le dosage spectrofluorimetrique (methode II) depend de l’extinction de la fluorescence native de l’eosine par les medicaments etudies, qui a ete mesuree a 540 nm apres excitation a 302 nm. Le trace spectrophotometrique. Le trace spectrophotometrique absorbance-concentration est lineaire sur les plages (1,0-5,0) et (1,0-10,0) μg/mL pour la bromhexine et l’ambroxol avec LOD de 0,31 et 0,14μg/mL et LOQ de 0,94 et 0,42μg/mL pour les deux medicaments respectivement. Le trace de la concentration fluorometrique est lineaire le long de la plage (1,0-5,0) μg/mL et (1-10) μg/mL pour les deux medicaments respectivement avec LOD de 0,13μg/mL et 0,22μg/mL et LOQ de 0,4μg/ mL et 0,65μg/mL pour les deux medicaments, respectivement. Les tests developpes ont ete valides en accord avec les recommandations de l’ICH et ils ont ete utilizes dans l’analyze des formulations de medicaments commerciaux contenant les deux medicaments mucolytiques et les resultats correspondaient a ceux obtenus par la methode de comparaison. In the experimental materials used by the author, we found trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride(cas: 23828-92-4COA of Formula: C13H19Br2ClN2O)

trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride(cas: 23828-92-4) is a medication indicated to alleviate chest congestion associated with conditions that include bronchitis, pneumonia, bronchospasm asthma, cough, and allergy.COA of Formula: C13H19Br2ClN2O Preclinically, ambroxol, the active ingredient of Mucosolvan, has been shown to increase respiratory tract secretion.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 329735-68-4On October 31, 2008 ,《Conversion of propargylic alcohols to β-oxo esters catalyzed by novel ruthenium-phosphoramidite complexes》 appeared in Advanced Synthesis & Catalysis. The author of the article were Costin, Stephen; Rath, Nigam P.; Bauer, Eike B.. The article conveys some information:

A series of half-sandwich phosphoramidite complexes of ruthenium were synthesized and employed as catalysts in the atom-economical formation of β-oxo esters from carboxylic acids and propargylic alcs. Reaction of the phosphoramidites (R)-BINOL-PNR2 (R = Me, 1a; i-Pr, 1b; benzyl, 1c) and (rac)-6,6′-dibromo-BINOL-PNMe2 (1d) with the dimeric p-cymene-ruthenium dichloride complex, [RuCl2(p-cymene)]2, gave the complexes [RuCl2(p-cymene)(L)] (L = 1a, 7a; 1b, 7b; 1c, 7c; 1d, 7d) in 96-66% yield. Accordingly, reaction of (R)-BINOL(8H)-PNMe2 (2a) and (R)-BINOL(8H)-PN(benzyl)2 (2b) with [RuCl2(p-cymene)]2 afforded the complexes [RuCl2(p-cymene)(L)] (L = 2a, 8a; 2b, 8b) in 82% and 86% yield. In a similar reaction, treatment of (R)-BIPHEN-PNMe2 (9) with [RuCl2(p-cymene)]2 gave the complex [RuCl2(p-cymene)(9)] (11) in 60% yield. Finally, phosphoramidite 1b reacted with [RuCl2(C6Me6)]2 to give [RuCl2(C6Me6)(1b)] (12) in 78% yield. All novel complexes are catalytically active in the formation of β-oxo esters from propargylic alcs. and carboxylic acids. Standard conditions involve cyclohexane solvent, propargylic alc. (1.0 equivalent), carboxylic acid (1.0 equivalent), ruthenium catalyst (1.5 mol%), and 90° for 5-18 h. Isolated yields of the β-oxo esters range from 87 to 16% and show broad substrate generality. The reaction proceeds without racemization if a chiral propargylic alc. is employed. The method is practical as no additives are required and the exclusion of oxygen and moisture is not needed. Complex 7c turned out to be the most effective catalyst (5 h reaction time), showing that the ligand structure has a profound impact on the catalytic performance. The crystal structure of 7a was determined, confirming an octahedral coordination geometry about the ruthenium center. The results came from multiple reactions, including the reaction of (R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4Application of 329735-68-4)

(R)-3,3′-Di-tert-butyl-5,5′,6,6′-tetramethylbiphenyl-2,2′-diol(cas: 329735-68-4) belongs to phenols. Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12).Application of 329735-68-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts