118017-20-2Relevant articles and documents
Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles
Mao, Biming,Xu, Yi,Chen, Yuehua,Dong, Jipan,Zhang, Junya,Gu, Kejia,Zheng, Bing,Guo, Hongchao
, p. 4424 - 4427 (2019)
A palladium-catalyzed asymmetric tandem [3+2] cycloaddition/allylation of methylene-trimethylenemethane is presented, providing the functionalized chiral hexahydropyrazolo[5,1-a]isoquinoline derivatives in high yields with good to excellent enantioselecti
A Convenient One-Pot Method for the Construction of Tetrasubstituted Phenols through a Michael Addition-Aldol Cyclization Sequence
Covarrubias-Zu?n?iga, Adria?n,Ri?os-Barrios, Eduardo
, p. 5688 - 5689 (1997)
The sodium salt of dimethyl 1,3-acetonedicarboxylate (1) readily reacts with certain alkynals under mild conditions in THF to give a tetrasubstituted aromatic ring with regiocontrol at the metaposition through a Michael addition-aldol cyclization sequence. Thus the reaction of I with propynal, 2-butynal, 2-pentynal, 2-octynal, 4-(benzoyloxy)-2-butynal, and 4-((tetrahydropyranyl)-oxy)-2-butynal at 25 °C gave the following products: dimethyl 2-hydroxybenzene-1,3-dicarboxylate (11percent), dimethyl 2-hydroxy-4-methylbenzene-1,3-dicarboxylate (45percent), dimethyl 4-ethyl-2-hydroxybenzene-1,3-dicarboxylate (46percent), dimethyl 2-hydroxy-4-pentylbenzene-1,3-dicarboxylate (42percent), dimethyl 2-hydroxy-4-((pivaloyloxy)methyl)benzene-1,3-dicarboxylate (88percent), dimethyl 2-hydroxy-4-((benzoyloxy)methyl)benzene-1,3-dicarboxylate (74percent), and dimethyl 2-hydroxy-4-(((tetrahydropyranyl)oxy)methyl)benzene-1,3-dicarboxylate (70percent).
Phosphodiester amidates of allenic nucleoside analogues: Anti-HIV activity and possible mechanism of action
Winter, Holger,Maeda, Yosuke,Mitsuya, Hiroaki,Zemlicka, Jiri
, p. 3300 - 3306 (1996)
Lipophilic phosphodiester amidates 2a, 2b, 4a, 4b, and 6 derived from anti-HIV agent adenallene 1a, 3a, inactive hypoxallene 1b, 3b, and 9-(4- hydroxy-2-butyn-1-yl)adenine (5) were synthesized and studied as inhibitors of HIV-1 in ATH8 cell system. All phosphodiester amidates were more biologically active than their parent nonphosphorylated compounds. Analogues 2a and 4a derived from (±)-adenallene 1a and (R)-enantiomer 3a are effective anti-HIV agents with EC50 approximately 0.88 and 0.21 μM, respectively. Both analogues are 16 and 28 times more effective than parent compounds 1a and 3a, respectively. Some anti-HIV activity of hypoxallene derivatives 2b and 4b was noted in the range of 0.1-10 μM but the dose- response relationship was poor. Phosphodiester amidate analogue 6 also exhibited anti-HIV activity in the range of 0.1-100 μM, but this effect was accompanied by cytotoxicity. Hydrolytic studies performed at pH 9.8 and with pig liver esterase at pH 7.4 have shown that analogue 2a gives adenallene 4'-phosphoralaninate (10a) as the major product. These results can be interpreted in terms of initial hydrolysis of phosphodiester amidates 2a, 2b, 4a, 4b, and 6 catalyzed by intracellular esterase(s) to give stable phosphomonoester amidate intermediates with a free carboxyl group. The results obtained with hypoxallene phosphoramidates 2b and 4b indicate that the aminosuccinate-fumarate enzyme system responsible for activation of AIDS drug ddIno (didanosine, Videx) can also, albeit less efficiently, activate hypoxallene 4'-phosphate (9b) and the respective (R)-enantiomer released inside the HIV-infected cells.
Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
Chen, Zhengwang,Wen, Yuelu,Fu, Yejuan,Chen, Hai,Ye, Min,Luo, Guotian
supporting information, p. 981 - 985 (2017/05/05)
Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro-ethane solvent with good catalytic activity.
Method for preparing hydroxamic acids
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Page/Page column 6, (2010/02/14)
Processes for using a compound of formula III: to make compounds of formulae I and II: and processes for making the compound of formula III, where R1-5 and J are as defined herein.
Use of hydrolases for the synthesis of cyclic amino acids
Lloyd, Richard C.,Lloyd, Michael C.,Smith, Mark E. B.,Holt, Karen E.,Swift, Jonathan P.,Keene, Philip A.,Taylor, Stephen J. C.,McCague, Raymond
, p. 717 - 728 (2007/10/03)
The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I
An efficient stereoselective synthesis of Z-(2S)- and Z-(2R)-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid, key intermediates in the synthesis of (2S,4S,5R)-(-)- and (2R,4R,5S)-(+)-bulgecinine
Holt, Karen E.,Swift, Jonathan P.,Smith, Mark E.B.,Taylor, Stephen J.C.,McCague, Raymond
, p. 1545 - 1548 (2007/10/03)
A concise, scaleable route to both isomers of Z-2-tert-butoxycarbonylamino-6-hydroxyhex-4-enoic acid from 2-butyne-1,4-diol, utilizing L- and D-acylase enzymes is presented. These intermediates were readily converted to multigram quantities of N-Boc-(2S,4
Subtype-selective NMDA receptor ligands and the use thereof
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, (2008/06/13)
The invention relates to subtype-selective NMDA receptor ligands and the use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neuro-degenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, Parkinson's disease, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.
Synthetic research on hepoxilins. 7.* Divergent total synthesis of hepoxilins and related eicosanoids
Mel'nikova,Vasil'eva,Pivnitsky
, p. 1199 - 1208 (2007/10/03)
A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-CICH2C≡CCHOHCH=CHCH2OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends altenatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.
