- Separation and identification of an impurity from the istradefylline intermediate
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Istradefylline is a selective adenosine antagonist for the A2a receptor, and it is used to treat the Parkinson's disease and improve dyskinesia in the early stage of the Parkinson's disease. An impurity in the istradefylline intermediate A1 (6-amino-1,3-diethyl-2,4-(1H,3H)-pyrimidinedione) was identified by high performance liquid chromatography (HPLC); it was separated by preparative HPLC and further characterized by UV, IR, MS, NMR, 2D NMR and single-crystal XRD analyses. The impurity was identified as (E)-N-ethyl-2-cyano-3-ethylamino-2-butenamide, which originated from the synthetic process of the intermediate A1. The structure of this impurity might affect the efficiency and safety of istradefylline; therefore, the research and control of this impurity are necessary for ensuring the quality of istradefylline.
- Meng, Zihui,Wang, Hongyi,Wang, Yiyun,Xu, Haojie,Xu, Zhibin,Xue, Min,Zheng, Zhonghui
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Read Online
- One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA
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Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.
- Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.
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- Design and synthesis of caffeic acid derivatives and evaluation of their inhibitory activity against Pseudomonas aeruginosa
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Bacteria need to transmit autoinducers to each other through a quorum sensing system. When the concentration of signal molecule reaches a threshold, it affects the expression of specific genes in bacteria, thereby improving the resistance of bacteria to antibiotics, promoting the formation of biofilms, and producing virulence factors. In this paper, various caffeic acid derivatives were synthesized based on functional groups. The results of growth curve and minimal inhibitory concentration proved that the derivatives did not affect the growth of Pseudomonas aeruginosa. Therefore, the inhibitory effects of the derivatives on biofilms and virulence factors were further evaluated. Among these derivatives examined, compound F-17 (4-bromophenethyl-3-(3, 4-dihydroxy-phenyl)acrylate) showed very significant inhibitory effect on biofilm, elastase, pyocyanin, and swarming motility. Molecular docking and calculation of binding free energy of F-17 also showed a good binding effect on LasR and PqsR. In addition, compound F-17 has no obvious cytotoxicity. These experimental results show that F-17 is a potential virulence factor inhibitor. [Figure not available: see fulltext.]
- Chen, Hong-geng,Chen, Wei-min,Liu, Wei-liang,Su, Ya-lun,Sun, Ping-hua,Zeng, Shao-gao,Zeng, Yun-feng,Zheng, Jun-xia,Zhou, Hai-bo
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p. 177 - 194
(2022/01/08)
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- Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues
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With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.
- Kulkarni, Mahesh R.,Lad, Nitin P.,Khedkar, Vijay M.,Gaikwad, Nitin D.
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p. 1359 - 1370
(2021/04/09)
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- In quest of small-molecules as potent non-competitive inhibitors against influenza
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A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.
- Malbari, Khushboo,Saha, Priyanka,Chawla-Sarkar, Mamta,Dutta, Shanta,Rai, Swita,Joshi, Mamata,Kanyalkar, Meena
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- Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles
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An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.
- Pan, Chunxiang,Yang, Chunhui,Li, Kangkui,Zhang, Keyang,Zhu, Yuanbin,Wu, Shiyuan,Zhou, Yongyun,Fan, Baomin
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supporting information
p. 7188 - 7193
(2021/10/01)
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- Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis
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Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.
- Fu, Ming-Chen,Fu, Yao,Shang, Rui,Wang, Ya-Ting,Zhao, Bin
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supporting information
p. 2495 - 2498
(2020/03/06)
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- New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation
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Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.
- Angeli, Andrea,Arifuddin, Mohammed,Singh, Priti,Supuran, Claudiu T.,Swain, Baijayantimala
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- Design, synthesis and biological evaluation of curcumin analogues as novel LSD1 inhibitors
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Histone lysine-specific demethylase 1 (LSD1) was the first discovered histone demethylase. Inactivating LSD1 or downregulating its expression inhibits cancer-cell development, and thus, it is an attractive molecular target for the development of novel cancer therapeutics. In this study, we worked on the structural optimization of natural products and identified 30 novel LSD1 inhibitors. Utilizing a structure-based drug design strategy, we designed and synthesized a series of curcumin analogues that were shown to be potent LSD1 inhibitors in the enzyme assay. Compound WB07 displayed the most potent LSD1 inhibitory activity, with an IC50 value of 0.8 μM. Moreover, WA20 showed an anticlonogenic effect on A549 cells with an IC50 value of 4.4 μM. Molecular docking simulations were also carried out, and the results indicated that the inhibitors bound to the protein active site located around the key residues of Asp555 and Asp556. These findings suggested that compounds WA20 and WB07 are the first curcumin analogue-based LSD1 inhibitors with remarkable A549 suppressive activity, providing a novel scaffold for the development of LSD1 inhibitors.
- Wang, Jiming,Zhang, Xiangyu,Yan, Jiangkun,Li, Wei,Jiang, Qinwen,Wang, Xinran,Zhao, Dongmei,Cheng, Maosheng
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supporting information
(2019/10/22)
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- Pyridazinone derivative, and preparation method and medical application thereof
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The invention provides a pyridazinone derivative, and a preparation method and a medical application thereof. O-formylbenzoic acid used as a raw material reacts with dimethyl phosphite to obtain dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate, the dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate reacts with 3-cyano-4-fluorobenzaldehyde in the presence of triethylamine to prepare (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile, and the (Z,E)-2-fluoro-5-[(3-oxoisobenzofuran-1(3H)-ylidene)methyl]benzonitrile is reduced by hydrazine hydrate to prepare 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid; and benzaldehyde or substituted aromatic formaldehyde or furfural used as a raw material and malonic acid undergo a Knoevenagel reaction to obtain cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid, the cinnamic acid or substituted cinnamic acid or furan-2-acrylic acid and 1-tert-butoxycarbonylpiperazine undergo an amidation reaction, a tert-butoxycarbonyl group is removed from the obtained amidation product in the presence of trifluoroacetic acid, and the obtained product and the 2-fluoro-5-[(4-oxo-3,4-dihydropyridazin-1-yl)methyl]benzoic acid undergo the amidation reaction to obtain a series of (E)-4-{3-[4-[(3-substituted aryl)acryloyl]piperazin-1-carbonyl]-4-fluorobenzyl}-2H-pyridazin-1-one derivatives. Results of preliminary pharmacological activity screening show that the compound represented by a general formula shown in the present invention has a certain in-vitro PARP-1 inhibition ability and a certain in-vitro tumor cell proliferation resisting activity. The structural general formula of compound is shown in the description; and in the general formula, Ar is selected from two formulas also shown in the description, and R1, R2, R3, R3, R4 and R5 can be the hydrogen atom, the fluorine atom, the chlorine atom, the bromine atom, a methyl group, a methoxy group, a tetrafluoromethyl group and a nitro group.
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Paragraph 0048-0052
(2019/10/07)
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- Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors
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A series of new Olaparib derivatives was designed and synthesized, and their inhibitory activities against poly (ADP-ribose) polymerases-1 (PARP-1) enzyme and cancer cell line MDA-MB-436 in vitro were evaluated. The results showed that compound 5l exhibited the most potent inhibitory effects on PARP-1 enzyme (16.10 ± 1.25 nM) and MDA-MB-436 cancer cell (11.62 ± 2.15 μM), which was close to that of Olaparib. As a PARP-1 inhibitor had been reported to be viable to neuroprotection, in order to search for new multitarget-directed ligands (MTDLs) for the treatment of Alzheimer’s disease (AD), the inhibitory activities of the synthesized compounds against the enzymes AChE (from electric eel) and BChE (from equine serum) were also tested. Compound 5l displayed moderate BChE inhibitory activity (9.16 ± 0.91 μM) which was stronger than neostigmine (12.01 ± 0.45 μM) and exhibited selectivity for BChE over AChE to some degree. Molecular docking studies indicated that 5l could bind simultaneously to the catalytic active of PARP-1, but it could not interact well with huBChE. For pursuit of PARP-1 and BChE dual-targeted inhibitors against AD, small and flexible non-polar groups introduced to the compound seemed to be conducive to improving its inhibitory potency on huBChE, while keeping phthalazine-1-one moiety unchanged which was mainly responsible for PARP-1 inhibitory activity. Our research gave a clue to search for new agents based on AChE and PARP-1 dual-inhibited activities to treat Alzheimer’s disease.
- Gao, Cheng-Zhi,Dong, Wei,Cui, Zhi-Wen,Yuan, Qiong,Hu, Xia-Min,Wu, Qing-Ming,Han, Xianlin,Xu, Yao,Min, Zhen-Li
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p. 150 - 162
(2018/11/30)
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- Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors
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Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.
- Ghafari, Shahrzad,Ranjbar, Sara,Larijani, Bagher,Amini, Mohsen,Biglar, Mahmood,Mahdavi, Mohammad,Bakhshaei, Maryam,Khoshneviszadeh, Mahsima,Sakhteman, Amirhossein,Khoshneviszadeh, Mehdi
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p. 978 - 985
(2019/06/13)
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- Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
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A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.
- Lu, Xiao-Yu,Li, Jin-Song,Wang, Shi-Qun,Zhu, Yu-Jing,Li, Yue-Ming,Yan, Lu-Yu,Li, Jia-Mei,Wang, Jin-Yu,Zhou, Hai-Pin,Ge, Xiu-Tao
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supporting information
p. 11123 - 11126
(2019/09/20)
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- Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents
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Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.
- Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling
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- Specific Residues Expand the Substrate Scope and Enhance the Regioselectivity of a Plant O-Methyltransferase
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An isoeugenol 4-O-methyltransferase (IeOMT), isolated from the plant Clarkia breweri, can be engineered to a caffeic acid 3-O-methyltransferase (CaOMT) by replacing three consecutive residues. Here we further investigated functions of these residues by constructing the triple mutant T133M/A134N/T135Q as well as single mutants of each residue. Phenolics with different chain lengths and different functional groups were investigated. The variant T133M improves the enzymatic activities against all tested substrates by providing beneficial interactions to residues which directly interact with the substrate. Mutant A134N significantly enhanced the regioselectivity. It is meta-selective or even specific against most of the tested substrates but para-specific towards 3,4-dihydroxybenzoic acid. The triple mutant T133M/A134N/T135Q benefits from these two mutations, which not only expand the substrate scope but also enhance the regioselectivity of IeOMT. On the basis of our work, regiospecific methylated phenolics can be produced in high purity by different IeOMT variants.
- Tang, Qingyun,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
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p. 3227 - 3233
(2019/07/04)
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- Total Synthesis and Evaluation of B-Homo Palmatine and Berberine Derivatives as p300 Histone Acetyltransferase Inhibitors
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Palmatine and berberine, structurally similar isoquinoline alkaloids exhibiting a broad range of biological activities, were recently found to inhibit p300 histone acetyltransferase (HAT), a potential therapeutic target for treating transcriptional activator-driven malignancies and diseases. Here, we report the first total synthesis of B-homo palmatine (11a) and berberine (11b) derivatives, which were synthesized from 3,4-dimethoxybenzaldehyde (1a) and benzo[d][1,3]dioxole-5-carbaldehyde (1b) in nine steps in 13.8 and 16.9 % overall yields, respectively. A number of other new B-homo palmatine and berberine derivatives were also prepared. These derivatives display good inhibitory activity against p300 HAT; compound 12a manifests the most potent inhibition with an IC50 value of 0.42 μm. Cell-based assays revealed that 12a exhibits certain inhibitory activity against HCG27, HT1080, and Z-138 cell lines, and no visible activity towards other cancer cell lines tested, reflecting that 12a has low cytotoxicity and acts against some types of cancer cells.
- Yang, Zhongzhen,Zhang, Yong,Chen, Xin,Li, Weijian,Li, Guo-Bo,Wu, Yong
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p. 1041 - 1052
(2018/03/06)
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- Analgesic effect of 5-(3,4-Dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one in experimental animal models of nociception
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Curcuminoids derived from turmeric rhizome have been reported to exhibit antinociceptive, antioxidant and anti-inflammatory activities. We evaluated the peripheral and central antinociceptive activities of 5-(3,4-dihydroxyphenyl)-3-hydroxy-1-(2-hydroxyphenyl)penta-2,4-dien-1-one (DHHPD), a novel synthetic curcuminoid analogue at 0.1, 0.3, 1 and 3 mg/kg (intraperitoneal), through chemical and thermal models of nociception. The effects of DHHPD on the vanilloid and glutamatergic systems were evaluated through the capsaicin- and glutamate-induced paw licking tests. Results showed that DHHPD significantly (p 0.05) attenuated the writhing response produced by the 0.8% acetic acid injection. In addition, 1 and 3 mg/kg of DHHPD significantly (p 0.05) reduced the licking time spent by each mouse in both phases of the 2.5% formalin test and increased the response latency of mice on the hot-plate. However, the effect produced in the latter was not reversed by naloxone, a non-selective opioid receptor antagonist. Despite this, DHHPD decreased the licking latency of mice in the capsaicin- and glutamate-induced paw licking tests in a dose response manner. In conclusion, DHHPD showed excellent peripheral and central antinociceptive activities possibly by attenuation of the synthesis and/or release of pro-inflammatory mediators in addition to modulation of the vanilloid and glutamatergic systems without an apparent effect on the opioidergic system.
- Kamarudin, Nadhirah,Hisamuddin, Nadia,Ong, Hui Ming,Ahmad Azmi, Ahmad Farhan,Leong, Sze Wei,Abas, Faridah,Sulaiman, Mohd Roslan,Shaik Mossadeq, Wan Mastura
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- A Simple and straightforward synthesis of cinnamic acids and ylidene malononitriles via knoevenagel condensation employing dabco as catalyst
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An efficient method for the synthesis of substituted cinnamic acid and ylidene malanonitriles is developed via Knoevenagel condensation of aromatic aldehydes with malonic acid and malononitrile in the presence of catalytic amounts of DABCO. This method has many advantages, such as mild reaction conditions, excellent yields, short reaction times and no furthur purification required.
- Nagalakshmi,Diwakar,Govindh,Gopal Reddy,Venu,Bhargavi,Prasanna Devi,Murthy,Siddaiah
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p. 1561 - 1564
(2017/05/29)
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- Enantioselective Synthesis of N?H-Free 1,5-Benzothiazepines
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An enantioselective sulfa-Michael-cyclization reaction was developed for the synthesis of 1,5-benzothiazepines with versatile pharmacological activities. The reaction between 2-aminothiophenol and α,β-unsaturated pyrazoleamides gave direct access to N?H-free 1,5-benzothiazepines in the presence of a chiral N,N′-dioxide/Yb(OTf)3complex. Excellent enantioselectivities (up to 96 % ee) and high yields (up to 99 %) were obtained for a broad range of substrates under mild reaction conditions. This method provided a facile approach to the antidepressant drug (R)-(?)-Thiazesim.
- Wang, Guojin,Tang, Yu,Zhang, Yu,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
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supporting information
p. 554 - 557
(2017/01/18)
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- Synthesis and biological evaluation of novel neoflavonoid derivatives as potential antidiabetic agents
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Various substituted neoflavonoid derivatives were synthesized using sulfated montmorillonite K-10 as a catalyst. This method is environmental friendly, sustainable and economical, convenient in isolation and purification processes, with little byproducts, using earth-abundant catalysts and has relatively high yield. Those neoflavonoid derivatives were screened for antioxidant, a-glucosidase inhibitory, aldose reductase 2 (ALR2) inhibitory and advanced glycation end-product formation inhibitory effects. Most compounds exhibited significant antioxidant and advanced glycation end-product (AGE) formation inhibitory activities. It was interesting to note that out of thirty compounds, 8k and 8l were found to have greater ALR2 inhibitory activity than the standard drug quercetin. The pharmacological studies suggested neoflavonoid with adjacent 7,8-dihydroxy groups were more effective in inhibiting ALR2. Antidiabetic activity studies had shown that compounds 8l and 8m were equipotent to the standard drug glibenclamide in vivo. In summary, the target compound 8l provided a potential drug design concept for the development of therapeutic or prophylactic agents of diabetes and diabetes complications.
- Wang, Bing,Li, Na,Liu, Teng,Sun, Jie,Wang, Xiaojing
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p. 34448 - 34460
(2017/07/22)
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- COMPOUNDS FOR INHIBITING LIPID OXIDATION AND A METHOD FOR PRODUCING THE SAME
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The present invention relates to a compound for inhibiting lipid oxidation, and a producing method thereof. The compound for inhibiting lipid oxidation is synthesized by a transesterification reaction though a vinyl reaction and a lipase-catalyzed reaction. The produced compound for inhibiting lipid oxidation has an excellent effect of inhibiting oxidation according to a total oxidation value (TOTOX) which is a combination of a P-anisidine value (P-AnV) and a peroxide value (PV) and an analysis of a thiobarbituric acid reaction substance (TBARS).COPYRIGHT KIPO 2016
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Paragraph 0135-0136; 0143
(2017/05/03)
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- Modular Approach to 9-Monosubstituted Fluorene Derivatives Using MoV Reagents
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Oxidative coupling using molybdenum(V) reagents provides fast access to highly functionalized 9-monosubstituted fluorenes. This synthetic approach is highly modular, is high yielding, and tolerates a variety of labile moieties, e.g. amides or iodo groups. The established protocol leads to promising precursors for pharmacologically important analogues of melatonin.
- Franzmann, Peter,Trosien, Simon,Schubert, Moritz,Waldvogel, Siegfried R.
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supporting information
p. 1182 - 1185
(2016/03/15)
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- Preparation method of neoflavonoids
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The invention relates to the field of chemical synthesis, in particular to a preparation method of neoflavonoids. The preparation method is characterized by comprising the following steps of using substituted benzaldehyde as an initial raw material to be reacted with malonic acid to generate a substituted phenylacrylic acid compound; performing an addition reaction, an elimination reaction and the like on the substituted phenylacrylic acid compound, or performing acetylation so as to protect a phenolic hydroxyl group, then performing a bromination reaction and the elimination reaction so as to synthesize the substituted phenylpropiolic acid compound ; and using montmorillonite K-10 after being acidulated by sulfuric acid as a catalyst, enabling the substituted phenylpropiolic acid compound and a phenolic compound to perform a heating reaction so as to generate the neoflavonoids. Compared with the prior art, the preparation method of the neoflavonoids, disclosed by the invention, has the characteristics that raw materials are cheap, and easy to obtain, the operation is simple, the catalyst can be recovered for use, and the method is environmentally-friendly, the post-treatment is simple, and the production cost is low, and the method has a high popularization and application value.
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Paragraph 0079; 0080
(2017/04/26)
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- Preparation method of 3,4-dihydro-4-arylcoumarin compounds
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The invention relates to the field of chemical synthesis, and concretely relates to a preparation method of 3,4-dihydro-4-arylcoumarin compounds. The method is characterized in that: substituted benzaldehyde is used as an initial raw material, propane diacid is added, a reaction is carried out with catalysis of piperidine, and substituted phenyl acrylic acid derivatives are obtained; montmorillonite K-10 which is acidified by sulfuric acid is used as a catalyst, a reaction between the substituted phenyl acrylic acid derivatives and phenolic compounds is carried out with heating, and the 3,4-dihydro-4-arylcoumarin compounds are obtained. Compared with the prior art, the preparation method of the 3,4-dihydro-4-arylcoumarin compounds has the advantages of easily available and cheap raw materials, simple operation, recyclable catalyst, environmental protection, simple post-treatment, low production cost, good promotion application, etc.
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Paragraph 0041
(2016/11/14)
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- Synthesis, characterization and nonlinear optical studies of novel blue-light emitting room temperature truxene discotic liquid crystals
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A new series of discotic liquid crystals based on a truxene core has been synthesized to study the structure-property relationship in view of the self-assembling property and their linear and nonlinear optical properties. All these branched alkyl chain truxene derivatives show a mesogenic property in a columnar hexagonal fashion at room temperature which is studied by a combination of different techniques. The newly synthesized truxene discotic 7a possesses a clearing temperature of 117 °C, one of the lowest clearing temperatures known in truxene discotic liquid crystals. We have discovered that the introduction of branching near to the core even in a small alkyl chain drastically reduces the isotropic temperature. Due to their C3 symmetry and their large first hyperpolarizability, these truxene derivatives show long-lived emissions in the solution state at room temperature. We also report large effective three-photon absorption in these materials under nanosecond laser pulse excitation at 532 nm, which makes them suitable candidates for optical limiting applications.
- Vinayakumara,Kumar, Manish,Sreekanth,Philip, Reji,Kumar, Sandeep
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p. 26596 - 26603
(2015/03/30)
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- THE 5,6-DIMETHOXY-1, 1-DIOXOBENZO(B)THIOPHENE-2-METHYLOXYCARBONYL (DM-BSMOC) AND RELATED AMINO-PROTECTING GROUPS
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Amino acid protecting groups are provided for use in peptide synthesis. Particular compounds disclosed include 5,6-dimethoxy-l,l-dioxobenzo[b]thiophi methyloxycarbonyl (DM-Bsmoc) and related amino-protecting groups.
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Page/Page column 13; 24
(2015/02/02)
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- Multifunctional novel Diallyl disulfide (DADS) derivatives with β-amyloid-reducing, cholinergic, antioxidant and metal chelating properties for the treatment of Alzheimer's disease
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A series of novel Diallyl disulfide (DADS) derivatives were designed, synthesized and evaluated as chemical agents, which target and modulate multiple facets of Alzheimer's disease (AD). The results showed that the target compounds 5a-l and 7e-m exhibited significant anti-Aβ aggregation activity, considerable acetylcholinesterase (AChE) inhibition, high selectivity towards AChE over butyrylcholinesterase (BuChE), potential antioxidant and metal chelating activities. Specifically, compounds 7k and 7l exhibited highest potency towards self-induced Aβ aggregation (74% and 71.4%, 25 μM) and metal chelating ability. Furthermore, compounds 7k and 7l disaggregated Aβ fibrils generated by Cu2+-induced Aβ aggregation by 80.9% and 78.5%, later confirmed by transmission electron microscope (TEM) analysis. Besides, 7k and 7l had the strongest AChE inhibitory activity with IC50 values of 0.056 μM and 0.121 μM, respectively. Furthermore, molecular modelling studies showed that these compounds were capable of binding simultaneously to catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. All the target compounds displayed moderate to excellent antioxidant activity with ORAC-FL values in the range 0.546-5.86 Trolox equivalents. In addition, absorption, distribution, metabolism and excretion (ADME) profile and toxicity prediction (TOPKAT) of best compounds 7k and 7l revealed that they have drug like properties and possess very low toxic effects. Collectively, the results strongly support our assertion that these compounds could provide good templates for developing new multifunctional agents for AD treatment.
- Manral, Apra,Saini, Vikas,Meena, Poonam,Tiwari, Manisha
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p. 6389 - 6403
(2015/10/05)
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- Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
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A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 μM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 μM and 9.6 ± 0.5 μM, respectively. A structure-activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.
- Leong, Sze Wei,Mohd Faudzi, Siti Munirah,Abas, Faridah,Mohd Aluwi, Mohd Fadhlizil Fasihi,Rullah, Kamal,Wai, Lam Kok,Abdul Bahari, Mohd Nazri,Ahmad, Syahida,Tham, Chau Ling,Shaari, Khozirah,Lajis, Nordin H.
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p. 16058 - 16081
(2015/01/08)
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- Improved synthesis of natural ester sintenin and its analogues via Wittig reaction
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The synthesis of a cytotoxic natural ester sintenin (7a) and twenty eight of its analogues including nitrogen-containing heterocyclic indole moiety (7b-7t), saturated (10a-10d) and unsaturated (10e-10h) amides were carried out by convenient route via one-pot Wittig reaction in aqueous medium with improved yield. A systematic structure activity relationship of sintenin ester was designed by chemically modified derivatives in order to get better cytotoxicity.
- Sharma, Mukul,Rajesh, U. Chinna,Rawat, Diwan S.
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p. 1853 - 1860
(2014/01/17)
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- Synthesis of a new urea derivative: A dual-functional organocatalyst for Knoevenagel condensation in water
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A phenylalanine-urea compound-catalyzed Knoevenagel condensation in water is reported. Various aldehydes and active methylene compounds undergo condensation at room temperature to give the desired products in high yields. The mechanism of the condensation of aldehydes with Meldrum's acid catalyzed by the novel urea derivative is also disclosed.
- Le, Wen-Jun,Lu, Hong-Fei,Zhou, Jun-Tao,Cheng, He-Long,Gao, Yu-Hua
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p. 5370 - 5373
(2013/09/12)
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- Triton-B adsorbed on flysh: An efficient support for the base catalysed reactions under microwave irradiations
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The application of Triton-B adsorbed on flyash (a waste material of thermal plants ) has been reported for the variety of base catalysed reactions such as synthesis of cinnamic acids by Deobner reaction, synthesis of 1-(2-hydroxyphenyl)-5-phenylpent-4-ene-1, 3-diones by Baker-Venkataraman reaction and synthesis of 3-carboxycoumarins by knoevenagel reaction. This material also acts as a support for the reaction and avoids the use of any solvent in the reaction maintaining the norms of Green Chemistry.
- Goel, Vijender
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p. 1725 - 1728
(2013/06/27)
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- The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
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The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that α,β-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents.
- Yang, Na,Wang, Qing-He,Wang, Wen-Qian,Wang, Jian,Li, Feng,Tan, Shen-Peng,Cheng, Mao-Sheng
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body text
p. 53 - 56
(2012/02/16)
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- C-1 alkynylation of N-methyltetrahydroisoquinolines through CDC: A direct access to phenethylisoquinoline alkaloids
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Direct cross-coupling between N-methyltetrahydroisoquinolines and alkynes using CuI-DEAD is presented. It affords the regioselective C-1-alkynylated products in good yield. This regio-selectivity is in contrast to the results reported earlier in the reaction of N,N-dimethylbenzyl amine where the N-methyl alkynylated product was formed exclusively or predominantly. The C-1-substituted propargylic isoquinolines were easily reduced to phenethylisoquinolines with Pd/C. This reaction sequence provides a short route to synthesize methopholine, homolaudanosine and other phenethylisoquinoline alkaloids. Georg Thieme Verlag Stuttgart · New York.
- Singh, Kamal Nain,Singh, Paramjit,Kaur, Amarjit,Singh, Pushpinder
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supporting information; experimental part
p. 760 - 764
(2012/07/02)
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- New greener alternatives for bioreduction of aromatic aldehydes and decarboxylation of aromatic acids using juice of fruits
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Cocos nucifera L. and Borassus flabellifer L. juices act as bio catalytic system for the reduction of aromatic aldehydes to alcohols and selective decarboxylation of substituted cinnamic acid to styrene and substituted benzoic acid to polyphenolic compound. Both juices exhibit good activity when aromatic aldehydes and aromatic acids contain electron-donating groups at specific positions. Moreover, C. nucifera juice exhibits good result for the reduction and decarboxylation properties than B. flabellifer juice under the same reaction condition.
- Misra, Kaushik,Maity, Himadri Sekhar,Chanda, Subhankar,Nag, Ahindra
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experimental part
p. 92 - 95
(2012/09/22)
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- OXADIAZOLE COMPOUNDS, THEIR PREPARATION AND USE
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The present invention relates to oxadiazole compounds in all their stereoisomeric and tautomeric forms and mixtures thereof in all ratios; and their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutically acceptable prodrugs and pharmaceutically acceptable polymorphs. The invention also relates to processes for the manufacture of the oxadiazole compounds and to pharmaceutical compositions containing them. The said compounds and their pharmaceutical compositions are useful in the treatment of cancer, particularly chronic myeloid leukemia (CML). The present invention further provides a method of treatment of cancer by administering a therapeutically effective amount of said compounds or their pharmaceutical compositions, to a mammal in need thereof.
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Page/Page column 60
(2011/09/30)
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- Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors
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Because of the complex cascade of molecular events that can occur in the brain of an Alzheimer's disease (AD) patient, the therapy of this neurodegenerative disease seems more likely to be achieved by multifunctional drugs. Herein, a new series of dual-targeting ligands have been developed and in vitro bioevaluated. Their architecture is based on conjugating the acetylcholinesterase inhibition and anti-oxidant properties in one molecular entity. Specifically, a series of naturally occurring phenolic acids with recognized anti-oxidant properties (derivatives of caffeic acid, rosmarinic acid, and trolox) have been conjugated with choline to account for the recognition by acetylcholinesterase (AChE). The synthesized hybrid compounds evidenced AChE inhibitory capacity of micromolar range (rationalized by molecular modeling studies) and good antioxidant properties. Their effects on human neuroblastoma cells, previously treated with beta-amyloid peptides and 1-methyl-4-phenylpyridinium ion neurotoxins (to simulate AD and Parkinson's disease, respectively), also demonstrated a considerable capacity for protection against the cytotoxicity of these stressors.
- Sebestik, Jaroslav,Marques, Sergio M.,Fale, Pedro L.,Santos, Susana,Arduino, Daniela M.,Cardoso, Sandra M.,Oliveira, Catarina R.,Serralheiro, M. Luisa M.,Santos, M. Amelia
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experimental part
p. 485 - 497
(2012/05/19)
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- Curcumin recognizes a unique binding site of tubulin
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Although curcumin is known for its anticarcinogenic properties, the exact mechanism of its action or the identity of the target receptor is not completely understood. Studies on a series of curcumin analogues, synthesized to investigate their tubulin binding affinities and tubulin self-assembly inhibition, showed that: (i) curcumin acts as a bifunctional ligand, (ii) analogues with substitution at the diketone and acetylation of the terminal phenolic groups of curcumin are less effective, (iii) a benzylidiene derivative, compound 7, is more effective than curcumin in inhibiting tubulin self-assembly. Cell-based studies also showed compound 7 to be more effective than curcumin. Using fluorescence spectroscopy we show that curcumin binds tubulin 32 ? away from the colchicine-binding site. Docking studies also suggests that the curcumin-binding site to be close to the vinblastine-binding site. Structure-activity studies suggest that the tridented nature of compound 7 is responsible for its higher affinity for tubulin compared to curcumin.
- Chakraborti, Soumyananda,Das, Lalita,Kapoor, Neha,Das, Amlan,Dwivedi, Vishnu,Poddar, Asim,Chakraborti, Gopal,Janik, Mark,Basu, Gautam,Panda, Dulal,Chakrabarti, Pinak,Surolia, Avadhesha,Bhattacharyya, Bhabatarak
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experimental part
p. 6183 - 6196
(2011/11/06)
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- Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives
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Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC50 values of 0.2, 2.0, 1.7, and 1.1 μM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.
- Zou, Hongbin,Wu, Hao,Zhang, Xiangnan,Zhao, Yu,St?ckigt, Joachim,Lou, Yijia,Yu, Yongping
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experimental part
p. 6351 - 6359
(2010/10/19)
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- Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation: Preparation of α,β-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands
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The optimal conditions to prepare α,β-unsaturated methyl esters via Wittig reaction combining polymer-assisted solution-phase synthesis (PASPS) methodology and simultaneous ultrasound and microwave irradiation were established. The effects of temperature, solvent, and irradiation time were discussed. Results clearly indicated the superiority of combined ultrasound and microwave-assisted procedure over microwave-assisted methodology. Moreover, an efficient PASPS procedure to prepare α,β-unsaturated carboxylic acids via tandem Wittig olefination and hydrolysis reaction was developed under combined ultrasound and microwave irradiation. Generally, a good conversion of aldehydes to acids was observed. The optimized protocols allowed us to quickly prepare a small collection of either α,β-unsaturated esters or carboxylic acids, key intermediates for the drug-discovery process of new sigma ligands. Copyright Taylor & Francis Group, LLC.
- Rossi,Urbano,Baraglia, A. Carnevale,Serra,Bergamelli,Iannelli,Azzolina,Collina
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p. 3254 - 3262
(2011/03/18)
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- Hydroxyapatite supported caesium carbonate as a new recyclable solid base catalyst for the Knoevenagel condensation in water
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The Knoevenagel condensation between aromatic aldehydes and malononitrile, ethyl cyanoacetate or malonic acid with hydroxyapatite supported caesium carbonate in water is described. HAP-Cs2CO3 was found to be a highly active, stable and recyclable catalyst under the reaction conditions.
- Gupta, Monika,Gupta, Rajive,Anand, Medha
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experimental part
(2010/04/22)
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- CO2 absorbing cost-effective ionic liquid for synthesis of commercially important alpha cyanoacrylic acids: A safe process for activation of cyanoacetic acid
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Cost-effective and carbon dioxide absorbing ionic liquid, tri-(2-hydroxyethyl) ammonium acetate, was shown to perform multiple roles in Knoevenagel condensation. It acted as an environmentally benign solvent, as an activating catalyst for the less reactive cyanoacetic acid and also as a risk reduction medium for the unevenly generated large amount of CO2 gas for large scale reactions. The reaction was scaled up for multi-gram synthesis of commercially important alpha cyanoacrylic acids.
- Sharma, Yogesh O.,Degani, Mariam S.
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scheme or table
p. 526 - 530
(2010/04/23)
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- Design and synthesis of novel 2-phenylaminopyrimidine (PAP) derivatives and their antiproliferative effects in human chronic myeloid leukemia cells
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A series of novel 2-phenylaminopyrimidine (PAP) derivatives structurally related to STI-571 were designed and synthesized. The abilities of these compounds to inhibit proliferation were tested in human chronic myeloid leukemia K562 cells. (E)-3-(2-bromophenyl)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2- ylamino)phenyl]acrylamide( 12d) was the most effective cell growth inhibitor and was 3-fold more potent than STI-571.
- Chang, Sheng,Yin, Shi-Liang,Wang, Jian,Jing, Yong-Kui,Dong, Jin-Hua
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experimental part
p. 4166 - 4179
(2009/12/28)
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- NEW PHARMACEUTICAL COMPOUNDS
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Compounds of formula (I), wherein R1-R4, X, Y and Z are as defined in claims, exhibit COMT enzyme inhibiting activity and are thus useful as COMT inhibitors.
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Page/Page column 17-18
(2008/06/13)
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- Dopamine D3 receptor antagonists. 1. Synthesis and structure-activity relationships of 5,6-Dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans
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5,6-Dimethoxy-2-(N-dipropyl)-aminoindan (3, PNU-99194A) was found to be a selective dopamine D3 receptor antagonist with potential antipsychotic properties in animal models. To investigate the effects of nitrogen substitution on structure- activity relationships, a series of 5,6-dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans were synthesized and evaluated in vitro for binding affinity and metabolic stability. The results indicate that substitution at the amine nitrogen of the 2-aminoindans is fairly limited to the di-N-propyl group in order to achieve selective D3 antagonists. Thus, combinations of various alkyl groups were generally inactive at the D3 receptor. Although substitution with an N-alkylaryl or N-alkylheteroaryl group yields compounds with potent D3 binding affinity, the D2 affinity is also enhanced, resulting in a less than 4-fold preference for the D3 receptor site, and no improvements in metabolic stability were noted. A large-scale synthesis of the D3 antagonist 3 has been developed that has proven to be reproducible with few purification steps. The improvements include the use of 3,4-dimethoxybenzaldehyde as a low-cost starting material to provide the desired 5,6-dimethoxy-1-indanone 5c in good overall yield (65%) and the formation of a soluble silyl oxime 17 that was reduced efficiently with BH3·Me2S. The resulting amino alcohol was alkylated and then deoxygenated using a Lewis acid and Et3SiH to give the desired product 3 in good overall yield of (～65%) from the indanone 5c.
- Haadsma-Svensson,Cleek,Dinh,Duncan,Haber,Huff,Lajiness,Nichols,Smith,Svensson,Zaya,Carlsson,Lin
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p. 4716 - 4732
(2007/10/03)
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- Synthesis of cinnamic acid derivatives using ethanol as solvent or microwave assisted method
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A comparison study about some parameters which influence the condensation of veratraldehyde with malonic acid in the presence of piperidine using ethanol as solvent and microwave irradiation was done, the obtainment of several substituted cinnamic acids are reported.
- Pellon,Mamposo,Gonzalez,Calderon
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p. 3769 - 3774
(2007/10/03)
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- ISOLATION OF HYPOXOSIDE FROM HYPOXIS ROOPERI AND SYNTHESIS OF (E)-1,5-BIS(3',4'-DIMETHOXYPHENYL)PENT-4-EN-1-YNE
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Isolation of the known diglucoside of (E)-1,5-bis(3',4'-dihydroxyphenyl)pent-4-en-1-yne (hypoxoside) from Hypoxis rooperi is described.In vivo tests indicate low toxic properties.A general synthesis for the introduction of the pentenyne link between two aromatic rings is described.Key words: Hypoxis rooperi; Hypoxidaceae; corms; hypoxoside; 1,5-diphenylpent-4-en-1-yne; rooperol; synthesis.
- Drewes, Siegfried E.,Hall, Alida J.,Learmonth, Robin A.,Upfold, Ursula J.
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p. 1313 - 1316
(2007/10/02)
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- NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING-II; GRIGNARD COUPLING OF HETEROCYCLIC COMPOUNDS
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A general, versatile method for alkylation and arylation of haloheterocyclic compounds is reported.In the presence of a catalytic quantity of , where dppp stands for Ph2P(CH2)3PPh2, bromothiophenes, halopyridines, haloquinoline, and haloisoquinolines reacted with alkyl and aryl Grignard reagents at room temperature or at ether refluxing temperature to give the cross-coupling products.The coupling reactions has been applied to the synthesis of isoquinoline alkaloids.Reactivities of 2-thienyl and 2-pyridyl Grignard reagents have also been examined.
- Tamao, K.,Kodama, S.,Nakajima, I.,Kumada, M.,Minato, A.,Suzuki, K.
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p. 3347 - 3354
(2007/10/02)
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