18457-55-1Relevant academic research and scientific papers
Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol
Wu, Xiang,Wang, Hai-Jun,Huang, Yong-Shuang,Li, Wei-Dong Z.
, p. 1871 - 1874 (2018)
Asymmetric total synthesis of (+)-sphaerodiol (2) has been achieved. A key step is an intramolecular [2 + 2] cycloaddition of alkyl(phenylthio)ketene for rapid assembly of the decalin ring.
Biomass to value added chemicals: Isomerisation of β-pinene oxide over supported ionic liquid catalysts (SILCAs) containing Lewis acids
Salminen, Eero,Rujana, Luis,M?ki-Arvela, P?ivi,Virtanen, Pasi,Salmi, Tapio,Mikkola, Jyri-Pekka
, p. 318 - 321 (2015)
The isomerisation of β-pinene oxide was studied over supported ionic liquid catalysts (SILCAs) consisting of Lewis acids in immobilized ionic liquid. SILCAs were demonstrated as efficient catalysts for the transformation of β-pinene oxide to myrtanal with the product distribution and activity being dependent on the nature of the ionic liquid and Lewis acid strength of catalytic species. With the catalyst ZnCl2/[N(3-OH-Pr)Py][NTf2]/ACC, the highest myrtanal molar yield obtained was 68%.
New hybrid compounds combining fragments of usnic acid and monoterpenoids for effective tyrosyl-dna phosphodiesterase 1 inhibition
Dyrkheeva, Nadezhda S.,Filimonov, Aleksandr S.,Luzina, Olga A.,Zakharenko, Alexandra L.,Ilina, Ekaterina S.,Malakhova, Anastasia A.,Medvedev, Sergey P.,Reynisson, Jóhannes,Volcho, Konstantin P.,Zakian, Suren M.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
, (2021/07/02)
Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabi-lized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cyto-toxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protec-tive” effect from topotecan on non-cancerous cells requires further investigation.
Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols
Shi, Chang-Yun,Yin, Liang,Zhang, Qi,Zhou, Si-Wei
supporting information, p. 26351 - 26356 (2021/11/09)
By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.
One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization
Brummel, Beau R.,Lee, Kinsey G.,McMillen, Colin D.,Kolis, Joseph W.,Whitehead, Daniel C.
, p. 9622 - 9627 (2019/12/02)
A novel technique for the absolute stereochemical determination of alcohols has been developed that uses crystallization of guanidinium salts of organosulfates. The simple one-pot, two-step process leverages facile formation of guandinium organosulfate single crystals for the straightforward determination of the absolute stereochemistry of enantiopure alcohols by means of X-ray crystallography. The strong hydrogen bonding network drives the stability of the crystal lattice and allows for a diverse range of organic alcohol substrates to be analyzed.
Perilla alcohol derivative and its preparation and use
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Paragraph 0025; 0026, (2018/04/02)
The invention belongs to the technical field of medicine, and relates to a series of perilla alcohol derivatives disclosed as Formula I, and preparation and application thereof. The invention also relates to pharmaceutically acceptable salts and solvates of the perilla alcohol derivatives, and a pharmaceutical composition containing the perilla alcohol derivatives or pharmaceutically acceptable salts thereof as active components, which can be used for treating cancers. The perilla alcohol derivatives and pharmaceutical salts thereof have favorable anticancer activity. The preparation method is simple and feasible, and is easy to operate.
Perilla amine compound and its preparation and use (by machine translation)
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Paragraph 0028; 0029, (2018/04/02)
The invention belongs to the field of medical technology, involves a series of formula I structure perilla amine compound and its preparation and use. The states the perilla amine compound includes pharmaceutically acceptable salts and solvates, and states the perilla amines containing the compound or its pharmaceutically acceptable salt as an active ingredient of the composition, can be used for treating cancer. The invention the perilla amine compounds and their pharmaceutically acceptable salts has better anti-cancer activity, its preparation method is simple and feasible, and easy to operate. (by machine translation)
Selective Base-free Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds using iPrOH or EtOH as Hydrogen Source
Farrar-Tobar, Ronald A.,Wei, Zhihong,Jiao, Haijun,Hinze, Sandra,de Vries, Johannes G.
supporting information, p. 2725 - 2734 (2018/02/28)
Commercially available Ru-MACHOTM-BH is an active catalyst for the hydrogenation of several functional groups and for the dehydrogenation of alcohols. Herein, we report on the new application of this catalyst to the base-free transfer hydrogenation of carbonyl compounds. Ru-MACHOTM-BH proved to be highly active and selective in this transformation, even with α,β-unsaturated carbonyl compounds as substrates. The corresponding aliphatic, aromatic and allylic alcohols were obtained in excellent yields with catalyst loadings as low as 0.1–0.5 mol % at mild temperatures after very short reaction times. This protocol tolerates iPrOH and EtOH as hydrogen sources. Additionally, scale up to multi-gram amounts was performed without any loss of activity or selectivity. An outer-sphere mechanism has been proposed and the computed kinetics and thermodynamics of crotonaldehyde and 1-phenyl-but-2-en-one are in perfect agreement with the experiment.
Hydrogenation and Reductive Amination of Aldehydes using Triphos Ruthenium Catalysts
Christie, Francesca,Zanotti-Gerosa, Antonio,Grainger, Damian
, p. 1012 - 1018 (2018/01/27)
An air-stable and readily accessible ruthenium dihydride complex catalyses aldehyde hydrogenation under neutral conditions. A high activity has been shown in a number of examples, and solvent-free conditions are also applicable, which favours industrial-scale applications. The catalyst has also been demonstrated to be active at low catalyst loadings for the reductive amination of aldehydes under mildly acidic conditions. A number of examples of chemoselectivity challenges are also presented in which the catalyst does not reduce carbon?halogen groups, alkene or ketone functionality. The advantage of using the pre-formed complex, Triphos-Ru(CO)H2 (1), over in situ formed catalysts from Triphos and Ru(acac)3 (acac=acetylacetonate) is also shown in terms of both chemoselectivity and activity, in particular this can be seen if low reaction temperatures are used.
Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives
Hui, Zi,Zhang, Meihui,Cong, Lin,Xia, Mingyu,Dong, Jinhua
, p. 6671 - 6682 (2014/06/10)
Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells comparing with that of (S)-perillyl alcohol. Among these derivatives, compounds VI5 and VI7 were the most potent agents, with the IC50s below 100 μM. It was demonstrated that the antiproliferative effect of VI5 was mediated through the induction of apoptosis in A549 cells.
