Tag: 100-200

Contrasting Anticancer Activity of Half-Sandwich Iridium(III) Complexes Bearing Functionally Diverse 2-Phenylpyridine Ligands was written by Millett, Adam J.;Habtemariam, Abraha;Romero-Canelon, Isolda;Clarkson, Guy J.;Sadler, Peter J.. And the article was included in Organometallics in 2015.COA of Formula: C6H6BrNO This article mentions the following:

We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η⁵-Cp*)Ir(2-(R’-phenyl)-R-pyridine)Cl] bearing either an electron-donating (-OH, -CH₂OH, -CH₃) or electron-withdrawing (-F, -CHO, -NO₂) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η⁵-Cp*)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η⁵-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) exhibit the expected “piano-stool” configuration. DFT calculations showed that substituents caused only localized effects on the electrostatic potential surface of the chelating 2-PhPy ligand of the complexes. Hydrolysis of all complexes is rapid, but readily reversed by addition of NaCl. The complexes show preferential binding to 9-ethylguanine over 9-methyladenine and are active catalysts for the oxidation of NADH to NAD⁺. Antiproliferative activity experiments in A2780 ovarian, MCF-7 breast, A549 lung, and HCT116 colon cancer cell lines showed IC₅₀ values ranging from 1 to 89 μM, with the most potent complex, [(η⁵-Cp*)Ir(2-(2′-methylphenyl)pyridine)Cl] (13) (A2780 IC₅₀ = 1.18 μM), being 10× more active than the parent, [(η⁵-Cp*)Ir(2-phenylpyridine)Cl], and 2× more active than [(η⁵-Cp^xPh)Ir(2-phenylpyridine)Cl]. Intriguingly, contrasting biol. activities are observed between structural isomers despite exhibiting similar chem. reactivity. For pairs of structural isomers both the nature and position of the functional group can affect the hydrophobicity of the complex. An increase in hydrophobicity resulted in enhanced cellular-iridium accumulation in A2780 ovarian cells, which generally gave rise to an increase in potency. The structural isomers [(η⁵-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) and [(η⁵-Cp*)Ir(2-phenyl-5-fluoropyridine)Cl] (4) preferentially localized in the cytosol > membrane and particulate > nucleus > cytoskeleton. This work highlights the strong dependence of biol. behavior on the nature and position of the substituent on the chelating ligand and shows how this class of organometallic anticancer complexes can be fine-tuned to increase their potency without using extended cyclopentadienyl systems. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-4-methanol (cas: 118289-16-0COA of Formula: C6H6BrNO).

2-Bromopyridine-4-methanol (cas: 118289-16-0) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.COA of Formula: C6H6BrNO

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Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution was written by Sekino, Tomoyuki;Sato, Shunta;Kuwabara, Kazuki;Takizawa, Koji;Yoshino, Tatsuhiko;Kojima, Masahiro;Matsunaga, Shigeki. And the article was included in Synthesis in 2020.Name: 2-(4-(Trifluoromethyl)phenyl)ethanol This article mentions the following:

Herein, allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated α-derivatization and subsequent cobalt-catalyzed allylic substitution was identified. The sequential transformations allow for highly regioselective access to branched allylic substitution products with a variety of aliphatic side chains RCH₂CH(CH=CH₂)CH(C(O)OR¹)₂ (R = Me, phenylmethyl, 2-thiophen-2-ylmethyl, etc.; R¹ = Me, Bn, 4-methylphenyl, etc.) and 2-(pent-1-en-3-yl)malononitrile. The photoredox-enabled cobalt catalysis is indispensable for achieving high yields and regioselectivity for the desulfonylative substitution in contrast to traditional metal-catalyzed protocols, which lead to inferior outcomes in the corresponding transformations. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Name: 2-(4-(Trifluoromethyl)phenyl)ethanol).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Name: 2-(4-(Trifluoromethyl)phenyl)ethanol

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Synthesis and Biological Evaluation of N-Hydroxyphenylacrylamides and N-Hydroxypyridin-2-ylacrylamides as Novel Histone Deacetylase Inhibitors was written by Thaler, Florian;Colombo, Andrea;Mai, Antonello;Amici, Raffaella;Bigogno, Chiara;Boggio, Roberto;Cappa, Anna;Carrara, Simone;Cataudella, Tiziana;Fusar, Fulvia;Gianti, Eleonora;di Ventimiglia, Samuele Joppolo;Moroni, Maurizio;Munari, Davide;Pain, Gilles;Regalia, Nickolas;Sartori, Luca;Vultaggio, Stefania;Dondio, Giulio;Gagliardi, Stefania;Minucci, Saverio;Mercurio, Ciro;Varasi, Mario. And the article was included in Journal of Medicinal Chemistry in 2010.Quality Control of 2-Bromopyridine-4-methanol This article mentions the following:

The histone deacetylases (HDACs) are able to regulate gene expression, and histone deacetylase inhibitors (HDACi) emerged as a new class of agents in the treatment of cancer as well as other human disorders such as neurodegenerative diseases. In the present investigation, we report on the synthesis and biol. evaluation of compounds derived from the expansion of a HDAC inhibitor scaffold having N-hydroxy-3-phenyl-2-propenamide and N-hydroxy-3-(pyridin-2-yl)-2-propenamide as core structures and containing a phenyloxopropenyl moiety, either unsubstituted or substituted by a 4-methylpiperazin-1-yl or 4-methylpiperazin-1-ylmethyl group. The compounds were evaluated for their ability to inhibit nuclear HDACs, as well as for their in vitro antiproliferative activity. Moreover, their metabolic stability in microsomes and aqueous solubility were studied and selected compounds were further characterized by in vivo pharmacokinetic experiments These compounds showed a remarkable stability in vivo, compared to hydroxamic acid HDAC inhibitors that have already entered clin. trials. The representative compound I showed in vivo antitumor activity in a human colon carcinoma xenograft model. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-4-methanol (cas: 118289-16-0Quality Control of 2-Bromopyridine-4-methanol).

2-Bromopyridine-4-methanol (cas: 118289-16-0) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Quality Control of 2-Bromopyridine-4-methanol

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A Facile and Efficient Anti-Selective Four-Component Direct Aldol Addition via Chemoselective Thioester Enolate Formation was written by Zhou, Guoqiang;Yost, Julianne M.;Sauer, Scott J.;Coltart, Don M.. And the article was included in Organic Letters in 2007.Reference of 29364-29-2 This article mentions the following:

A facile and efficient four-component anti-selective direct aldol addition of thioester enolates was developed that is fully compatible with enolizable aldehydes and able to be conducted using untreated reagent-grade CH₂Cl₂ open to the air. The thioester enolates were generated in situ via an acylation/conjugate addition sequence using com. available PhSLi and acryloyl chloride, thus avoiding prior enolate formation while maintaining complete chemoselectivity. For example, 88 % (13:1 anti:syn) S-Ph 3-hydroxy-3-phenyl-2-[(phenylthio)methyl]propanethioate was obtained from PhCHO, acryloyl chloride and PhSLi in the presence of MgBr₂·Et₂O in CH₂Cl₂ open to the air. The organosulfur products are convertible into various polyketide-based structures. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Reference of 29364-29-2).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Reference of 29364-29-2

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Alcohol – Wikipedia,
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Thermochemical liquefaction of Brassica napus straw: Effect of liquefaction parameters on biocrude was written by Xiao, Zhihua;Wu, Qingdan;Zheng, Xiaochen;Zhang, Liqing;Zou, Dongsheng;Chen, Baoxiong;Wang, Bin;Liu, Fen. And the article was included in Industrial Crops and Products in 2022.Reference of 499-75-2 This article mentions the following:

Rape straw (Brassica napus) was used to prepare high-quality biocrude (ORS) through thermochem. liquefaction. The effects of liquefaction temperature, solid-liquid ratio (R1), and solvent filling ratio (R2) on the yield of ORS prepared from rape straw were studied. The yield of ORS reached the maximum value (22.11 %) at 340 °C, with R1 10 % and R2 20 %. GC-MS anal. indicated that at low liquefaction temperatures (>300 °C) the compounds in ORS were mainly esters, whereas at higher temperatures they were mainly phenolic compounds Anal. based on the b.ps. indicated the presence of mainly C8, C9, and C20 compounds Elemental anal. and measurement of the higher heating value (HHV) showed that the HHV of ORS at 340 °C was 41.36 MJ/kg. The process described in this work not only effectively disposes of rape straw, but also converts it into a potential renewable transportation energy alternative. In the experiment, the researchers used many compounds, for example, 5-Isopropyl-2-methylphenol (cas: 499-75-2Reference of 499-75-2).

5-Isopropyl-2-methylphenol (cas: 499-75-2) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Reference of 499-75-2

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Alcohol – Wikipedia,
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Potentially tridentate hydrazonic ligands in the synthesis of methyl and acetyl palladium(II) complexes was written by Pelagatti, Paolo;Carcelli, Mauro;Franchi, Francesca;Pelizzi, Corrado;Bacchi, Alessia;Fochi, Andrea;Fruhauf, Hans-Werner;Goubitz, Kees;Vrieze, Kees. And the article was included in European Journal of Inorganic Chemistry in 2000.Quality Control of 6-Methyl-2-pyridinemethanol This article mentions the following:

Potentially tridentate hydrazonic ligands HNNO (HL1-HL5) were used in the synthesis of some Me Pd(II) complexes. Depending on the applied exptl. conditions two different kinds of complexes were obtained. Thus, the reactions between HL1-HL5 and (COD)PdMeCl in Et₂O gave bidentate Me complexes Pd(HNN)MeCl (1–5; shown as I; R’/R”/R”’ = H/Me/Me, H/Me/Ph, H/H/Ph, H/Et/Ph, Me/H/Ph), where the ligands maintain a neutral character. However, in the presence of a base such as Et₃N or NaOMe, the ligands are deprotonated with the consequent formation of tridentate Me complexes Pd(NNO)Me (7–10; shown as II). In solution, complexes 1–5 tend to lose the hydrazonic proton with elimination of methane and formation of a tridentate chloride complex Pd(NNO)Cl; this tendency can be correlated with the acidity of the free ligands, which was determined On bubbling CO through solutions of 1–5, the corresponding acetyl complexes Pd(HNN)[C(O)Me]Cl (11–15) formed, in which both the cis and trans isomers are present. Their molar ratio is rationalized from the results of a mol. modeling study from electronic considerations. A remarkably different reactivity was found in the carbonylation of the tridentate complexes 7–10; they decompose rapidly and quant. to Pd black and an organic product corresponding to the ligand with an acetyl group bonded to the hydrazonic N. The x-ray structures of a Me complex (3) and its corresponding acetyl (13) derivative were determined In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Quality Control of 6-Methyl-2-pyridinemethanol).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Quality Control of 6-Methyl-2-pyridinemethanol

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Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The effects of α-pinene versus toluene-derived secondary organic aerosol exposure on the expression of markers associated with vascular disease was written by Lund, Amie K.;Doyle-Eisele, Melanie;Lin, Ying-Hsuan;Arashiro, Maiko;Surratt, Jason D.;Holmes, Tom;Schilling, Katherine A.;Seinfeld, John H.;Rohr, Annette C.;Knipping, Eladio M.;McDonald, Jacob D.. And the article was included in Inhalation Toxicology in 2013.Category: alcohols-buliding-blocks This article mentions the following:

To investigate the toxicol. effects of biogenic- vs. anthropogenic-source secondary organic aerosol (SOA) on the cardiovascular system, the Secondary Particulate Health Effects Research program irradiation chamber was used to expose atherosclerotic apolipoprotein E null (Apo E-/-) mice to SOA from the oxidation of either α-pinene or toluene for 7 days. SOA atmospheres were produced to yield 250-300 μg/m³ of particulate matter and ratios of 10:1:1 α-pinene:nitrogen oxide (NO_x):ammonia (NH₃); 10:1:1:1 α-pinene:NO_x:NH₃:sulfur dioxide (SO₂) or 10:1:1 toluene:NO_x:NH₃; and 10:1:1:1 toluene:NO_x:NH₃:SO₂. Resulting effects on the cardiovascular system were assessed by measurement of vascular lipid peroxidation (thiobarbituric acid reactive substance (TBARS)), as well as quantification of heme-oxygenase (HO)-1, endothelin (ET)-1, and matrix metalloproteinase (MMP)-9 mRNA expression for comparison to previous program exposure results. Consistent with similar previous studies, vascular TBARS were not increased significantly with any acute SOA exposure. However, vascular HO-1, MMP-9, and ET-1 observed in Apo E-/- mice exposed to α-pinene + NO_x + NH₃ + SO₂ increased statistically, while α-pinene + NO_x + NH₃ exposure to either toluene + NO_x + NH₃ or toluene +NO_x + NH₃ + SO₂ resulted in a decreased expression of these vascular factors. Such findings suggest that the specific chem. created by the presence or absence of acidic components may be important in SOA-mediated toxicity in the cardiovascular system and/or progression of cardiovascular disease. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Category: alcohols-buliding-blocks).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Development of a magnetic MoS2 system camouflaged by lipid for chemo/phototherapy of cancer was written by Li, Jiaqian;Yang, Na;Yang, Mei;Lu, Chao;Xie, Meng. And the article was included in Colloids and Surfaces, B: Biointerfaces in 2022.Application of 111-46-6 This article mentions the following:

Untargeted release of traditional chemotherapeutic drugs can damage normal tissues in the body and cause serious side effects for patients. Therefore, the research of targeted drug delivery system based on nanomaterials has become a hot topic in the field of cancer therapy. Magnetic molybdenum disulfide (mMoS2) was modified by liposomes with a cell membrane-like structure to prepare nanocarrier complex (mMoS2-Lipid) with high biocompatibility and stability. Then, combined photo-chemotherapeutic therapy was realized both in vitro and in vivo by its ultra-high photothermal conversion efficiency and excellent drug loading profile of mMoS2-Lipid. The characterization showed that the lamellar magnetic molybdenum disulfide modified by liposomes was not easy to aggregate in physiol. solution, and had a lower non-specific protein adsorption rate, which was beneficial for biomedical application. In vitro cell experiments exhibited a successful cellular uptake profile of MCF-7 cells with no significant cytotoxicity, while a concentration dependent cytotoxicity for both chemotherapy alone and photo-chemotherapy combined therapy. Compared with the unmodified mMoS2, mMoS2-Lipid injected into mice through tail vein can accumulate more in the tumor site, and in vivo anti-tumor studies have shown that the synergistic treatment of the mMoS2-Lipid has an obvious inhibitory effect on the tumor with less toxic and side effects on mice. In conclusion, mMoS2-Lipid treatment system provides a safe, rapid and effective choice for the treatment of breast cancer in the future. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Application of 111-46-6).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Application of 111-46-6

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High Tensile Strength UV-Cured Castor Oil-Based Silicone-Modified Polyurethane Acrylates was written by Jiao, Xiaojiao;Song, Yan;He, Na;Wang, Xiaojia;Huang, Ming;Zhang, Lu;Li, Xiaocheng;Xu, Jinchang;Chen, Jie;Li, Wenqing;Lai, Guoqiao;Hua, Xilin;Yang, Xiongfa. And the article was included in ACS Omega in 2022.Safety of 2,2′-Oxybis(ethan-1-ol) This article mentions the following:

High tensile strength UV-cured transparent materials are highly desired in optical devices. In this paper, high tensile strength UV-cured transparent castor oil-based polyurethane acrylates (PUAs) with a very high transmittance over 95% (400-800 nm) were prepared from UV-curable castor oil-based polyurethane acrylates (CO-PUAs) and mercapto silicone-containing hyperbranched polymers (HBPSHs) under UV irradiation The tensile strengths of UV-cured transparent castor oil-based PUAs can reach 12.49 MPa, which is obviously higher than that of UV-cured CO-PUAs reported previously (0.7-10.20 MPa). The chem. structure of HBPSHs will play an important role in the mech. performance of UV-cured silicone-modified materials, and it can be concluded that the more rigid the units of α,β-dihydroxyl derivatives used in the fabrication of HBPSHs are, the higher the mech. strength and pencil hardness of the UV-cured materials will be. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Safety of 2,2′-Oxybis(ethan-1-ol)).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Safety of 2,2′-Oxybis(ethan-1-ol)

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A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative was written by Lambert, Kyle M.;Kelly, Christopher B.;Milligan, John A.;Tilley, Leon J.;Reynolds, Robert P.;McGuire, Kellen P.;Anzalone, Luigi;Del Sesto, Kimberly E.;Walsh, Sinead. And the article was included in Journal of Chemical Education in 2022.Formula: C7H7ClO This article mentions the following:

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chem. courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chem. textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor’s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a com. available oxoammonium salt (Bobbitt’s salt) to cleanly oxidize cinnamyl alc. to cinnamaldehyde. In addition to being a safe, convenient, colorimetric and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II or advanced laboratory sections alike, and can be completed within a standard 3-4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of ¹H NMR, ¹³C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Formula: C7H7ClO).

(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Formula: C7H7ClO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts