- Production process of 2, 6-dimethylphenoxyacetic acid
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The invention discloses a production process of 2, 6-dimethylphenoxyacetic acid, and belongs to the technical field of organic chemical industry. The upstream product 2, 6-dimethyl phenoxy acetic acidof 2, 6-dimethyl phenoxy acetyl chloride is prepared by controlling the two steps of substitution reaction and ester hydrolysis reaction, and the prepared 2, 6-dimethyl phenoxy acetic acid is high inpurity, does not generate large impurities, and is beneficial to subsequent preparation of lopinavir.
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Paragraph 0018-0032
(2021/03/31)
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- Formation of calix[4]arenes with acyloxycarboxylate functions
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Calix[4]arenes are an exciting class of multifunctional compounds. Their ability to bind small molecules and ions actively makes them useful tools for many applications. While looking for a suitable chelating agent, a particular modification of the calix[4]arene led to an unexpected side reaction. In this work, we will describe the selective formation of the observed acyloxyacetate derivatives. The according yields can be regulated by controlling the water content of the solvent system. All new compounds were obtained in yields higher than 45percent and fully characterized by NMR, MS, EA, and X-ray crystallography. By performing and analyzing several reactions with different calix[4]arenes and monomeric derivatives, an explanation for the reaction mechanism was postulated. Further, we report on the modification of reaction conditions which were investigated to verify our findings’ veracity. In total, three acyloxyacetate derivatives were synthesized and characterized to support our conclusions.
- Bauer, David,Stipurin, Sergej,K?ckerling, Martin,Mamat, Constantin
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- Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration
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Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.
- Matralis, Alexios N.,Xanthopoulos, Dimitrios,Huot, Geneviève,Lopes-Paciencia, Stéphane,Cole, Charles,de Vries, Hugo,Ferbeyre, Gerardo,Tsantrizos, Youla S.
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supporting information
p. 5547 - 5554
(2018/10/15)
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- Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed-Ligand Copper(I) Complex
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The catalytic activity of the mixed-ligand copper(I) complex [Cu(PPh3)2(κ2-O,O"-lact)] (1) {lact = l-(+)-lactate} has been investigated in carbene transfer and carbene insertion reactions. Complex 1 catalytically promoted the diastereoselective cyclopropanation of olefins in the presence of ethyl diazoacetate (EDA), under mild conditions, and with a low catalyst loading (1 mol-%). In the case of internal alkenes, a trans/cis ratio of up to 93:7 was reached. Moreover, compound 1 easily promoted the insertion of the carbene fragment deriving from the decomposition of ethyl diazoacetate into O–H (alcohols and phenols) and N–H (amine) bonds, with formation of the corresponding ethyl 2-alkoxyacetate, ethyl 2-phenoxyacetate, and ethyl 2-aminoacetate derivatives in good to high yields.
- Brenna, Stefano,Ardizzoia, G. Attilio
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p. 3336 - 3342
(2018/07/13)
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- Synthesis and Herbicidal Activity of Some Novel Pyrazole Derivatives
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Some novel pyrazole derivatives were designed and synthesized through multi-step reactions from substituted phenol as starting material. Their structures were confirmed by 1H NMR, FTIR, MS and elemental analysis. All these compounds were evaluated their herbicidal activity. The preliminary bioassay results indicated that some of title compounds displayed moderate herbicidal activity at 200 μg/mL. Among them, compounds 4-chloro-N'-(2-(2,5-dimethyl-phenoxy) acetyl)-3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-N'-(2-(2,4-dichlorophenoxy)acetyl)- 3-ethyl-1-methyl-1H-pyrazole-5-carbohydrazide, 4-chloro-3-ethyl-1-methyl-N'-(2-(m-tolyloxy) acetyl)-1H-pyrazole-5-carbohydrazide and 4-chloro-3-ethyl-1-methyl-N'-(2-(3-nitrophenoxy)acetyl)- 1H-pyrazole-5-car-bohydrazide possessed 95%, 100%, 95% and 95% inhibition against Brassica campestris respectively. In the further bioassay, the compound 6l exhibited excellent herbicidal activity either monocotyledon or dicotyledon plant at 150 g/ha.
- He, Hai-Qin,Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia
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p. 195 - 200
(2017/07/22)
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- SALICYLIC ACID DERIVATIVE COMPOUND AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
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The present invention provides the salicylic acid derivative compound or its pharmaceutically acceptable salt useful for treating several diseases, a pharmaceutical composition containing the compound or its salt, and a treating or preventing method using the compound or its salt. The salicylic acid derivative compound of the present invention has suppressing effect on excitatory toxicity, anti-oxidant effect, cell-protecting effect, anti-inflammatory effect, etc. and can be effectively used for treating or preventing brain neuronal disease such as amyotrophic lateral sclerosis, Parkinson' s disease, Huntington' s disease, Alzheimer' s disease, stroke, traumatic brain injury and traumatic spinal cord injury; ocular disease such as glaucoma, diabetic retinopathy and macular degeneration; pain disease such as neuropathic pain; and inflammatory disease such as arteriosclerosis, gastritis, colitis, arthritis, nephritis, hepatitis, cancer and degenerative disease.
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Page/Page column 44-45
(2008/06/13)
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- Inhibitors of aspartyl protease
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The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.
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- Retroviral protease inhibiting compounds
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A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.
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- Synthesis and structure-activity relationships of a novel series of HIV-1 protease inhibitors encompassing ABT-378 (Lopinavir)
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The HIV protease inhibitor ABT-378 (Lopinavir) has a 2,6-dimethylphenoxyacetyl group in the P-2′ position. Analogues in which this group is replaced with various substituted phenyl or heteroaryl groups were synthesized and the structure-activity relationships explored.
- Sham, Hing L.,Betebenner, David A.,Chen, Xiaoqi,Saldivar, Ayda,Vasavanonda, Sudthida,Kempf, Dale J.,Plattner, Jacob J.,Norbeck, Daniel W.
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p. 1185 - 1187
(2007/10/03)
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- 2',6'-Dimethylphenoxyacetyl: A new achiral high affinity P3-P2 ligand for peptidomimetic-based HIV protease inhibitors
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Starting from palinavir (1), our lead HIV protease inhibitor, we have discovered a new series of truncated analogues in which the P3-P2 quinaldic-valine portion of 1 was replaced by 2',6'-dimethylphenoxyacetyl. With EC50's in the 1-2 nM range, some of these compounds are among the most potent inhibitors of HIV replication in vitro, reported to date. One of the most promising members in this series (compound 27, BILA 2185 BS) exhibited a favorable overall pharmacokinetic profile, with 61% apparent oral bioavailability in rat. X-ray crystal structures and molecular modeling were used to rationalize the high potency resulting from incorporation of this structurally simple, achiral ligand into the P3-P2 position of hydroxyethylamine-based HIV protease inhibitors.
- Beaulieu, Pierre L.,Anderson, Paul C.,Cameron, Dale R.,Croteau, Gilbert,Gorys, Vida,Grand-Ma?tre, Chantal,Lamarre, Daniel,Liard, Francine,Paris, William,Plamondon, Louis,Soucy, Fran?ois,Thibeault, Diane,Wernic, Dominik,Yoakim, Christiane,Pav, Susan,Tong, Liang
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p. 1094 - 1108
(2007/10/03)
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- RETROVIRAL PROTEASE INHIBITING COMPOUNDS
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A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.
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- Relationship between anticonvulsant activity and enzyme inhibitory effectiveness of substituted oxadiazoles
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Eight 2-(2,6-dimethylphenoxymethyl)-5-arylamino-1,3,4-oxadiazoles were synthesized. All oxadiazoles (100 mg/kg, ip) possessed anticonvulsant activity. This was reflected by 10-60% protection observed against pentylenetetrazol (90 mg/kg, sc)-induced convulsions in mice. All oxadiazoles also inhibited in vitro respiratory activity of rat brain homogenates. The antiproteolytic activity of these oxadiazoles was reflected by their ability to provide protection against in vitro trypsin-induced hydrolysis of bovine serum albumin and this ranged from 21% to 44% at a final concentration of 0.5 mM. All oxadiazoles (2 mM) inhibited in vitro succinate dehydrogenase activity of rat brain homogenates and the degree of inhibition ranged from 25-86%.
- Chaudhary,Chaudhary,Parmar,et al.
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p. 105 - 110
(2007/10/02)
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- Anticonvulsant activity and selective inhibition of NAD dependent oxidations in rat brain homogenates by newer mercaptotriazoles
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Eight 1-(2,6-dimethylphenoxyacetyl)-4-(substituted phenyl)thiosemicarbazides were cyclized to the corresponding 5-(2,6-dimethylphenoxymethyl)-4-(substituted phenyl)-3-mercapto-1,2,-4(4H)-triazoles and 5-(2,6-dimethylphenoxymethyl)-4-(substituted phenyl)-3-[1,2,4(4H)-triazolethioglycolic] acids. These compounds were characterized by their sharp melting points, elemental analyses, and IR spectra and were evaluated for anticonvulsant activity. The degree of protection (range) provided by these thiosemicarbazides, triazoles, and triazolethioglycolic acids at a dose of 100 mg/kg ip against pentylenetetrazol (90 mg/kg sc)-induced convulsions in mice was 10-50, 20-80, and 10-70%, respectively, where cyclization to triazoles increased anticonvulsant activity of the precursor thiosemicarbazides. Increased protection by these compounds against convulsions was generally associated with decreased 24-hr pentylenetetrazol-induced mortality. These compounds exhibited selective in vitro inhibition of nicotinamide adenine dinucleotide (NAD)-dependent oxidation of pyruvate, α-ketoglutarate, and NADH by rat brain homogenates while NAD-independent oxidation of succinate remained unaltered. The presence of added NAD to the reaction mixture during in vitro oxidation of pyruvic acid not only increased the respiratory activity of rat brain homogenates but also decreased the inhibitory effectiveness of thiosemicarbazides, triazoles, and triazolethioglycolic acids. The degree of selective inhibition of NAD-dependent oxidations was unrelated to their anticonvulsant activity.
- Parmar,Chaudhary,Chaudhary,Kumar,Spiro
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p. 971 - 975
(2007/10/09)
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