Month: January 2023

Synthesis and biological evaluation of novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs) as high active anti-HIV agents was written by He, Yan-Ping;Long, Jin;Zhang, Shui-Shuan;Li, Cong;Lai, Christopher Cong;Zhang, Chun-Sheng;Li, Da-Xiong;Zhang, De-Hua;Wang, Hua;Cai, Qing-Qing;Zheng, Yong-Tang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

A novel dihydro-aryl/alkylsulfanyl-cyclohexylmethyl-oxopyrimidines (S-DACOs), e.g., I, combinatory library was synthesized and evaluated with C8166 cells infected by the HIV-1_IIIB in vitro, using Nevirapine (NVP) and Zidovudine (AZT) as pos. control. The anti-HIV screening results revealed that C-6-cyclohexylmethyl substituted pyrimidinones possessed higher selective index than its 6-arylmethyl counterparts. Some compounds showed potent anti-HIV activities with EC₅₀ values of 0.012 to 0.162 nM. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Recommanded Product: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An NMR investigation of ground-state polarization of some substituted aromatic systems was written by Collins, Michael J.;Hatton, Paul M.;Sternhell, Sever. And the article was included in Australian Journal of Chemistry in 1992.Recommanded Product: 5-Methyl-2-nitrobenzonitrile This article mentions the following:

A previously established NMR method for estimating mobile bond orders was used to examine the ground-state polarization of benzene or heteroaromatic derivatives with ortho or para pairs of +R/-R substituents in benzene, naphthalene, furan, thiophene, pyrrole, quinoline, and pyrazole systems. Evidence for significant ground-state polarization which is solvent-independent was observed in these systems, especially benzene, pyrrole, and pyrazole. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Recommanded Product: 5-Methyl-2-nitrobenzonitrile).

5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 5-Methyl-2-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

multifunctional use of heterogeneous catalyst from littered Tectona grandis leaves towards sustainable biodiesel and chemical production was written by Gohain, Minakshi;Laskar, Khairujjaman;Phukon, Hridoyjit;Bora, Utpal;Kalita, Dipul;Deka, Dhanapati. And the article was included in Waste Management (Oxford, United Kingdom) in 2020.Recommanded Product: 55490-87-4 This article mentions the following:

Waste biomass derived heterogeneous catalyst is an excellent alternative to chem. synthesized catalysts. In this work, calcined Tectona grandis leaves were proposed as an eco-friendly, renewable and low cost heterogeneous base catalyst. The prepared catalyst was examined by FTIR, XRD, XPS, SEM, EDX, TEM, TGA, BET and Hammett indicator test. The catalyst has an appealing nature towards various chem. transformations due to its basic surface sites provided by alkali and alk. earth metals. The efficiency of the catalyst was successfully investigated by its application in biodiesel production The products were confirmed by ¹H and ¹³C NMR. 100% FAME conversion was attained using a catalyst loading of 2.5 wt% under optimized reaction parameters. The catalyst was further explored for Knoevenagel condensation reaction, in which it showed its effectiveness and recyclability towards the formation of benzylidenemalononitrile derivatives of aryl aldehydes. Thus, it is a potential ‘green catalyst’ derived from waste biomass without any addition of chems. that can replace the industrial base catalysts used for biodiesel production and Knoevenagel reaction and makes the protocol environmentally benign. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Asymmetric transfer hydrogenation of ketones catalyzed by rhenium complexes with chiral ferrocenylphosphane ligands was written by Mejia, Esteban;Aardoom, Raphael;Togni, Antonio. And the article was included in European Journal of Inorganic Chemistry in 2012.Electric Literature of C9H9NO This article mentions the following:

A series of new rhenium complexes containing chiral ferrocenyldiphosphine ligands, I (R = Ph, Cy; R¹ = Cy, 1-adamantyl, 3,5-(CF₃)₂C₆H₃, 3,5-Me₂C₆H₃) of the Josiphos family, starting from com. available rhenium sources. These new Re^V oxido and nitrido complexes, several of which have been characterized by x-ray crystallog., are air- and moisture-stable and are active catalysts in the asym. transfer hydrogenation of ketones using 2-propanol as the hydrogen source in the presence of substoichiometric amounts of triethylamine (TEA). The reaction proceeds cleanly with good to excellent yields (50-99 %) but with moderate enantioselectivity (up to 58 % ee). A mechanism not involving hydridic species is proposed. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Electric Literature of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Electric Literature of C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly Enantioselective Hydrosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion was written by Kang, Byung Chul;Shin, Sung Ho;Yun, Jaesook;Ryu, Do Hyun. And the article was included in Organic Letters in 2017.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile This article mentions the following:

A highly enantioselective hydrosilylation of ketones was developed for the synthesis of a variety of chiral secondary alcs. In the presence of a chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded with good yields (up to 99%) with excellent enantioselectivities (up to 99% ee). In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of (R)-4-(1-Hydroxyethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Potent and highly selective DP1 antagonists with 2,3,4,9-tetrahydro-1H-carbazole as pharmacophore was written by Li, Lianhai;Beaulieu, Christian;Carriere, Marie-Claude;Denis, Danielle;Greig, Gillian;Guay, Daniel;O’Neill, Gary;Zamboni, Robert;Wang, Zhaoyin. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H9NO This article mentions the following:

It was discovered that the introduction of a Me group to the benzylic position of the N-benzyl group in lead compound I has a dramatic effect on improving the binding selectivity of this ligand for the prostanoid receptors DP1 (receptor for prostaglandin D₂) as compared to TP (receptor for thromboxane A₂). Based on this discovery, a series of potent and highly selective DP1 antagonists have been synthesized. Among them, compound II was identified as a highly selective DP1 antagonist with excellent overall properties. It has a K_i of 0.43 nM to DP1 in binding assay and an IC₅₀ of 2.5 nM in the DP1 functional assay. Its selectivity for DP1 over TP (the most potent receptor after DP1) exceeds 750-fold based on both binding and functional assays. These properties make II a very potent and highly selective DP1 receptor antagonist suitable for investigating the biol. functions of DP1 in normal physiol. and models of disease. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Formula: C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Formula: C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pressure-induced emission enhancement of a series of dicyanovinyl-substituted aromatics: pressure tuning of the molecular population with different conformations was written by Wang, Qian;Li, Shayu;He, Liming;Qian, Yan;Li, Xiuping;Sun, Wenhao;Liu, Min;Li, Juan;Li, Yi;Yang, Guoqiang. And the article was included in ChemPhysChem in 2008.Recommanded Product: 55490-87-4 This article mentions the following:

Dicyanovinyl-substituted aromatic compounds (Ar-DCV; Ar = 9-anthracenyl, 1-naphthyl, 1-pyrenyl) with dual fluorescence are prepared, and their emission properties-when molecularly dispersed in a polymer medium-are studied under pressure perturbation. The total emission intensity is enhanced drastically from ambient pressure up to 70 kbar. Emission 30-107 times more intense than that at ambient pressure is observed at higher pressure. In dual emission, the enhancement of the local excited state (LE state) is significantly different from that of the intramol. charge-transfer state (ICT state). The intensity of the ICT emission increases faster (30-370 times) than that of the LE emission (<20 times). In accordance with spectroscopic data, emission dynamics at different pressures, and computational studies on the mol. conformations of these compounds, a kinetic model is proposed to explain the effect of pressure on the emissive properties of the Ar-DCV compounds from the point of view of pressure-dependent populations of the species in the ground state. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Recommanded Product: 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Recommanded Product: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

9-Amino-1,2,3,4-tetrahydroacridin-1-ols. Synthesis and evaluation as potential Alzheimer’s disease therapeutics was written by Shutske, Gregory M.;Pierrat, Frank A.;Kapples, Kevin J.;Cornfeldt, Michael L.;Szewczak, Mark R.;Huger, Francis P.;Bores, Gina M.;Haroutunian, Vahram;Davis, Kenneth L.. And the article was included in Journal of Medicinal Chemistry in 1989.Safety of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The synthesis of a series of 9-amino-1,2,3,4-tetrahydroacridin-1-ols is reported. These compounds are related to tacrine. They inhibit acetylcholinesterase in vitro and are active in a model that may be predictive of activity in Alzheimer’s disease; the scopolamine-induced impairment of 24-h memory of a passive dark-avoidance paradigm in mice. Two compounds, (±)-9-amino-1,2,3,4-tetrahydroacridin-1-ol maleate (HP-029) and (±)-9-(benzylamino)-1,2,3,4-tetrahydroacridin-1-ol maleate (HP-128), were also active in reversing the deficit in 72-h retention of a (1-trial dark-avoidance task in rats, induced by ibotenic acid lesions in the nucleus basalis magnocellularis. In addition, HP-128 showed potent in vitro inhibition of the uptake of radiolabeled noradrenaline and dopamine (IC₅₀ = 0.070 μM and 0.30 μM, resp.). HP-029 and HP-128, which showed less acute toxicity in both rats and mice than tacrine, are in phase II and phase I clin. trials, resp., for Alzheimer’s disease. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Safety of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Safety of 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Crown cation complex effects. 10. Potassium tert-butoxide mediated penultimate oxidative hydrolysis of nitriles was written by DiBiase, Stephen A.;Wolak, Raymond P. Jr.;Dishong, Dennis M.;Gokel, George W.. And the article was included in Journal of Organic Chemistry in 1980.Electric Literature of C8H13N This article mentions the following:

The failure of phase-transfer catalysis to improve either the yield or rapidity of basic nitrile hydrolysis is due, in part, to the poor solubility of quaternary ammonium hydroxides in nonpolar solutions An alternative hydrolysis method which involves KOCMe₃ mediated oxidative cleavage of the nitrile with loss of the cyano carbon is presented. The isolated yields range from 21-93% and are highest for long-chain aliphatic nitriles such as cyanohexadecane. Other compounds that underwent oxidative hydrolysis were PhCH₂CN, cyclohexaneacetonitrile, and cyclododecanecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Electric Literature of C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Electric Literature of C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and biological evaluation of novel pyrazolo[1,5-a]pyrimidines: Discovery of a selective inhibitor of JAK1 JH2 pseudokinase and VPS34 was written by Singleton, Justin D.;Dass, Reuben;Neubert, Nathaniel R.;Smith, Rachel M.;Webber, Zak;Hansen, Marc D. H.;Peterson, Matt A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.COA of Formula: C8H5Cl2N This article mentions the following:

A series of novel 3,6-di-substituted or 3-substituted pyrazolo[1,5-a]pyrimidines were prepared via a microwave-assisted approach that generated a broad array of derivatives in good yields (20-93%, ave. = 59%). The straightforward synthesis involved sequential treatment of com.-available acetonitrile derivatives with DMF-dimethylacetal (120°C, 20 min), followed by treatment with NH₂NH₂·HBr (120°C, 20 min), and 1,1,3,3-tetramethoxypropane or 2-aryl-substituted malondialdehdyes (120°C, 20 min). Compounds were screened for antimitotic activities against MCF7 breast cancer and/or A2780 ovarian cancer cell lines in vitro. The most active compounds exhibited EC₅₀ values ranging from 0.5 to 4.3μM, with the 3-(4-(trifluoromethyl)phenyl)-6-[4-(2-(piperidin-1-yl)ethoxy)]phenyl analog and the 3-(2-fluorophenyl)-6-[4-(2-(4-methylpiperizin-1-yl)ethoxy)]phenyl analog being two to three fold more active than Compound C (Dorsomorphin) in A2780 and MCF7 assays, resp. Importantly, a monosubstituted 3-(benzothiazol-2-yl) derivative was equipotent with the more synthetically challenging 3,6-disubstituted derivatives, and exhibited a promising and unique selectivity profile when screened against a panel consisting of 403 protein kinases (Kinomescan selectivity score = 0.005, K_d = 0.55 ± 0.055μM and 0.410 ± 0.20μM for JAK1 JH2 pseudokinase and VPS34, resp.). In the experiment, the researchers used many compounds, for example, 2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9COA of Formula: C8H5Cl2N).

2-(2,3-Dichlorophenyl)acetonitrile (cas: 3218-45-9) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).COA of Formula: C8H5Cl2N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts