132617-10-8Relevant articles and documents
Insecticidal activity of cyanohydrin and monoterpenoid compounds
Peterson, Chris J.,Tsao, Rong,Eggler, Aimee L.,Coats, Joel R.
, p. 648 - 654 (2000)
The insecticidal activities of several cyanohydrins, cyanohydrin esters and monoterpenoid esters (including three monoterpenoid esters of a cyanohydrin) were evaluated. Topical toxicity to Musca domestica L. adults was examined, and testing of many compounds at 100 μg/fly resulted in 100% mortality. Topical LD50 values of four compounds for M. domestica were calculated. Testing of many of the reported compounds to brine shrimp (Artemia franciscana Kellog) resulted in 100% mortality at 10 ppm, and two compounds caused 100% mortality at 1 ppm. Aquatic LC50 for values were calculated for five compunds for larvae of the yellow fever mosquito (Aedes aegypti (L.)). Monoterpenoid esters were among the most toxic compounds tested in topical and aquatic bioassays.
Diastereoselective and enantiospecific synthesis of γ-substituted α,β-unsaturated nitriles from O-protected allylic cyanohydrins
Baeza, Alejandro,Casas, Jesus,Najera, Carmen,Sansano, Jose M.
, p. 3837 - 3848 (2006)
γ-Functionalized α,β-unsaturated nitriles are prepared diastereoselectively and enantiospecifically from enantioenriched cyanohydrin-O-phosphates and carbonates derived from α,β-unsaturated aldehydes, either by palladium or iridium-catalyzed nucleophilic
CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**
Juhl, Martin,Petersen, Allan R.,Lee, Ji-Woong
supporting information, p. 228 - 232 (2020/11/30)
Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.
Highly chemoselective and efficient Strecker reaction of aldehydes with TMSCN catalyzed by MgI2 etherate under solvent-free conditions
He, Kailun,Liu, Huijun,Zhang, Xingxian,Zhou, Jing
supporting information, p. 933 - 936 (2019/03/08)
Strecker reaction of various substituted aromatic aldehydes, heteroaromatic aldehydes, aliphatic aldehydes and α,β-unsaturated aldehydes with trimethylsilyl cyanide (TMSCN) was realized in the presence of 5 mol % of MgI2 etherate in a mild, efficient and highly chemoselective manner under solvent-free conditions.
Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins
Jangir, Nisha,Padhi, Santosh Kumar
, p. 32 - 40 (2018/11/27)
Hydroxynitrile lyase (HNL) catalyzed enantioselective C–C bond formation is an efficient approach to synthesize chiral cyanohydrins which are important building blocks in the synthesis of a number of fine chemicals, agrochemicals and pharmaceuticals. Immobilization of HNL is known to provide robustness, reusability and in some cases also enhances activity and selectivity. We optimized the preparation of immobilization of Baliospermium montanum HNL (BmHNL) by cross linking enzyme aggregate (CLEA) method and characterized it by SEM. Optimization of biocatalytic parameters was performed to obtain highest % conversion and ee of (S)-mandelonitrile from benzaldehyde using CLEA-BmHNL. The optimized reaction parameters were: 20 min of reaction time, 7 U of CLEA-BmHNL, 1.2 mM substrate, and 300 mM citrate buffer pH 4.2, that synthesized (S)-mandelonitrile in ～99% ee and ～60% conversion. Addition of organic solvent in CLEA-BmHNL biocatalysis did not improve in % ee or conversion of product unlike other CLEA-HNLs. CLEA-BmHNL could be successfully reused for eight consecutive cycles without loss of conversion or product formation and five cycles with a little loss in enantioselectivity. Eleven different chiral cyanohydrins were synthesized under optimal biocatalytic conditions in up to 99% ee and 59% conversion, however the % conversion and ee varied for different products. CLEA-BmHNL has improved the enantioselectivity of (S)-mandelonitrile synthesis compared to the use of purified BmHNL. Nine aldehydes not tested earlier with BmHNL were converted into their corresponding (S)-cyanohydrins for the first time using CLEA-BmHNL. Among the eleven (S)-cyanohydrins syntheses reported here, eight of them have not been synthesized by any CLEA-HNL. Overall, this study showed preparation, characterization of a stable, robust and recyclable biocatalyst i.e. CLEA-BmHNL and its biocatalytic application in the synthesis of different (S)-aromatic cyanohydrins.
Design, synthesis, and in vitro evaluation of epigoitrin derivatives as neuraminidase inhibitors
Meng, Fanli,Yin, Yan,Lu, Cheng,Duan, Yongbin,Zhu, Yaohua,Huang, Chen,Zhou, Yiming,Xu, Xu,Wu, Fanhong
, p. 2037 - 2046 (2018/09/06)
Abstract: Influenza is an infectious disease which results in numerous epidemics every year. At present, neuraminidase is regarded, as the key therapeutic target against influenza and several well-known neuraminidase inhibitors are widely used as anti-influenza drugs. Combined computational methods including 3D-QSAR and molecular docking were applied to explore the structural–activity relationship with Xu’s compounds as the data set. Ten epigoitrin derivatives were then designed based on the computational results and they displayed 11.1–85.5?μM inhibitory potencies against neuraminidase in the in vitro biological evaluation. The combined computational studies did not only present the structural–activity relationship of Xu’s inhibitors, but also guide the designation of epigoitrin derivatives as novel neuraminidase inhibitors. Graphical abstract: [Figure not available: see fulltext.].
Aminoalcohol neuraminidase inhibitors, and preparation method thereof
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Paragraph 0031; 0035, (2017/09/01)
The invention discloses aminoalcohol neuraminidase inhibitors, and a preparation method thereof. The method concretely comprises the following steps: 1, reacting cinnamaldehyde, lithium perchlorate LiClO4.3H2O and trimethylsilyl cyanide (TMSCN) to obtain cyan analog; 2, reducing the cyan analog under the action of a reducing agent and an additive in order to obtain hydroxyl-substituted amino compounds; 3, reacting the hydroxyl-substituted amino compounds with acyl chloride under an alkaline condition to obtain one neuraminidase inhibitor; and 4, reacting the hydroxyl-substituted amino compounds with substituted benzyl bromide under an alkaline condition to obtain another one neuraminidase inhibitor with another structure. The compounds synthesized in the invention have novel structures, and have good neuraminidase activity.
Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding
Deng, Hui,Kooijman, Sander,Van Den Nieuwendijk, Adrianus M. C. H.,Ogasawara, Daisuke,Van der Wel, Tom,Van Dalen, Floris,Baggelaar, Marc P.,Janssen, Freek J.,Van Den Berg, Richard J. B. H. N.,Den Dulk, Hans,Cravatt, Benjamin F.,Overkleeft, Herman S.,Rensen, Patrick C. N.,Van der Stelt, Mario
supporting information, p. 428 - 440 (2017/04/26)
Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoylglycerol (2-AG) that activates cannabinoid CB1 receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4-substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5-position of the piperidine ring provided ultrapotent inhibitor 38 (DH376) with picomolar activity. Compound 38 temporarily reduces fasting-induced refeeding of mice, thereby emulating the effect of cannabinoid CB1-receptor inverse agonists. This was mirrored by 39 (DO34) but also by the negative control compound 40 (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple molecular targets.
Regio- and Stereospecific C- and O-Allylation of Phenols via φ-Allyl Pd Complexes Derived from Allylic Ester Carbonates
Discolo, Christopher A.,Graves, Alexander G.,Deardorff, Donald R.
, p. 1034 - 1045 (2018/06/18)
Two complementary strategies have been developed for the C- and O-allylation of phenols via a common φ-allyl Pd complex. While O-allylation of phenols by this method is a well-recognized reaction of general utility, the associated para-selective C-allylation reaction is still in its infancy. Cationic φ-allyl Pd intermediates, derived from allylic ester carbonates and palladium(0) catalyst, were found to undergo the Friedel-Crafts-type para-selective C-allylations with nine different phenols. Both C- and O-allylated products were obtained in good to excellent yields following a metal-catalyzed regio- and stereospecific substitutive 1,3-transposition. Conditions were also identified that control access to either allylated product. Finally, a study of the equilibrium established between the two allylation products revealed that the O-allylated compound was the kinetic product and the C-allylated compound the thermodynamic product.
Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex
Kim, Kicheol,Moeljadi, Adhitya Mangala Putra,Hirao, Hajime,Hong, Soon Hyeok
supporting information, p. 3292 - 3298 (2017/09/06)
Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).
