- Metabolically stable vanillin derivatives for the treatment of hypoxia
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Vanillin derivative compounds that bind covalently with hemoglobin are provided. Methods of treating sickle cell disease and other hypoxia-related disorders by administering such compounds are also provided.
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Page/Page column 12-14
(2021/09/01)
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- I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines
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A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.
- An, Zhenyu,Ren, Yi,Liu, Yafeng,Yan, Rulong
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supporting information
p. 2614 - 2617
(2021/08/06)
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- An investigation of structure‐activity relationships of azolylacryloyl derivatives yielded potent and long‐acting hemoglobin modulators for reversing erythrocyte sickling
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Aromatic aldehydes that bind to sickle hemoglobin (HbS) to increase the protein oxygen affinity and/or directly inhibit HbS polymer formation to prevent the pathological hypoxia‐induced HbS polymerization and the subsequent erythrocyte sickling have for s
- Abdulmalik, Osheiza,El‐araby, Moustafa E.,Ghatge, Mohini S.,Muhammad, Yosra A.,Omar, Abdelsattar M.,Paredes, Steven D.,Safo, Martin K.
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- Design and synthesis of novel breast cancer therapeutic drug candidates based upon the hydrophobic feedback approach of antiestrogens
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Based upon hydrophobic feedback approaches, we designed and synthesized novel sulfur-containing ERα modulators (4 and 5) as breast cancer therapeutic drug candidates. The tetrahydrothiepine derivative 5a showed the highest binding affinity toward ERα beca
- Ohta, Kiminori,Kaise, Asako,Taguchi, Fumi,Aoto, Sayaka,Ogawa, Takumi,Endo, Yasuyuki
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- Synthesis and Evaluation of 2-Azetidinone and 1H-Pyrrole-2,5-dione Derivatives as Cholesterol Absorption Inhibitors for Reducing Inflammation Response and Oxidative Stress
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Excess lipid accumulation can initiate the development and progression of atherosclerotic lesions, thus eventually leading to cardiovascular disease. Lipid-lowering medication therapy is one of the cornerstones of cardiovascular disease therapy. On the basis of the cholesterol absorption inhibitor ezetimibe, we successfully synthesized seven 2-azetidinone derivatives and eighteen 1H-pyrrole-2,5-dione derivatives. Most of the new compounds significantly inhibited cholesterol uptake in vitro. In addition, one of the most active inhibitors, 3-(4-fluorophenyl)-1-[(3S)-3-hydroxy-3-(4-hydroxyphenyl)propyl]-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione (14q), showed no cytotoxicity in L02 and HEK293T cell lines. Further evaluation indicated that 14q inhibited considerably the amount of TNF-α, ROS, MDA, and LDH in vitro. Therefore, 14q might be a novel cholesterol absorption inhibitor.
- Xia, Yineng,Zhu, Lijuan,Yuan, Xinrui,Wang, Yubin
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- Probing the mechanism of thermally driven thiol-Michael dynamic covalent chemistry
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The kinetics and mechanism of the thermally activated dynamic covalent exchange of thiol-Michael adducts is investigated. A model system of thiol-Michael adducts between thiophenol and phenylvinylketone derivatives and adducts between 2-mercaptoethanol phenylvinylketone derivatives in N,N-dimethylformamide (DMF) at elevated temperatures is used to probe the underlying exchange mechanism. The kinetic data show negligible free Michael acceptor, which is consistent with the highly efficient thiol-Michael reaction being a "click"-like reaction that significantly favors the adduct form. At elevated temperatures of 90 °C in DMF the thiol-Michael adducts reach equilibrium after 24 h, although equilibration did not occur within 24 h at 60 °C or 75 °C, and negligible exchange occurs under ambient conditions. A kinetic model was developed to describe the dynamic covalent exchange and equilibration. The experimental and simulation kinetic data of dynamic covalent exchange are consistent with the thiol-Michael adducts undergoing a retro-Michael reaction, followed by subsequent addition of a free thiol to the liberated Michael acceptor. Kinetic analysis is consistent with the fragmentation, or retro-Michael reaction, being the rate-determining step in the dynamic covalent exchange. This suggests that the key step in dynamic covalent exchange is not enhanced by addition of free thiol or free Michael acceptor, since the addition reaction is much faster than the retro-Michael reaction. This fundamental study will guide the design of organic compounds, materials, and bioconjugates that utilize the thermally activated dynamic covalent thiol-Michael linkages.
- Zhang, Borui,Chakma, Progyateg,Shulman, Max P.,Ke, Jun,Digby, Zachary A.,Konkolewicz, Dominik
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p. 2725 - 2734
(2018/04/26)
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- Method for preparing 5-hydroxyl-1-indanone
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The invention provides a method for preparing 5-hydroxyl-1-indanone. The method comprises the following steps: dissolving anisole and 3-chloropropionyl chloride into dichloromethane; under catalysis of a lewis acid catalyst of a multi-component mixture Al
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Paragraph 0035; 0037; 0038; 0039; 0041
(2018/10/19)
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- Asymmetric Hydrogenation of β-Secondary Amino Ketones Catalyzed by a Ruthenocenyl Phosphino-oxazoline-ruthenium Complex (RuPHOX-Ru): The Synthesis of γ-Secondary Amino Alcohols
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A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX-Ru) was applied successfully to the asymmetric hydrogenation of β-secondary amino ketones, directly affording the corresponding chiral γ-secondary amino alcohols in up to 99% yield and with 99% ee. Reaction with β-(benzylamino)-1-phenylpropan-1-one could be performed on a gram-scale with a relatively low catalyst loading (up to 2000 S/C). The resulting hydrogenated product could be used for the synthesis of synthetically useful compounds.
- Wang, Jianxia,Wang, Yanzhao,Liu, Delong,Zhang, Wanbin
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supporting information
p. 3262 - 3272
(2015/11/03)
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- Copper(II)-catalyzed hydrosilylation of ketones using chiral dipyridylphosphane ligands: Highly enantioselective synthesis of valuable alcohols
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In the presence of PhSiH3 as the reductant, the combination of enantiomeric dipyridylphosphane ligands and Cu(OAc)2·H 2O, which is an easy-to-handle and inexpensive copper salt, led to a remarkably practical and versatile chiral catalyst system. The stereoselective formation of a selection of synthetically interesting β-, γ- or δ-halo alcohols bearing high degrees of enantiopurity (up to 99.9 % enantiomeric excess (ee)) was realized with a substrate-to-ligand molar ratio (S/L) of up to 10 000. The present protocol also allowed the hydrosilylation of a diverse spectrum of alkyl aryl ketones with excellent enantioselectivities (up to 98 % ee) and exceedingly high turn-over rates (up to 50 000 S/L molar ratio in 50 min reaction time) in air, under very mild conditions, which offers great opportunities for the preparation of various physiologically active targets. The synthetic utility of the chiral products obtained was highlighted by the efficient conversion of optically enriched β-halo alcohols into the corresponding styrene oxide, β-amino alcohol, and β-azido alcohol, respectively.
- Yu, Feng,Zhou, Ji-Ning,Zhang, Xi-Chang,Sui, Yao-Zong,Wu, Fei-Fei,Xie, Lin-Jie,S. C. Chan, Albert,Wu, Jing
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supporting information; experimental part
p. 14234 - 14240
(2012/01/12)
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- Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification
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An enantioselective synthesis of chiral γ-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing γ-azidoalcohols in high enantiomeric excess.
- Kamal, Ahmed,Malik, M. Shaheer,Shaik, Ahmad Ali,Azeeza, Shaik
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p. 1078 - 1083
(2008/09/19)
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- Synthesis and binding properties of dendritic oxybathophenanthroline ligands towards copper(II)
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Dendritic oxybathophenanthroline ligands (generation 0 to 3) have been synthesized by treatment of 4,7-bis(4′-hydroxyphenyl)-1,10-phenanthroline with the corresponding Frechet-type dendrons carrying a benzylic bromide function at the focal point. The comp
- Stephan, Holger,Geipel, Gerhard,Bernhard, Gert,Comba, Peter,Rajaraman, Gopalan,Hahn, Uwe,Voegtle, Fritz
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p. 4501 - 4508
(2007/10/03)
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- Octahedral Fe(II) and Ru(II) complexes based on a new bis 1,10-phenanthroline ligand that imposes a well defined axis
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A bis-chelating ligand (L1), made of two 7-(p-anisyl)-1,10-phenanthroline (phen) subunits connected with a p-(CH2)2C6H4 (CH2)2 spacer through their 4 positions, has been prepared, using Skr
- Pomeranc,Heitz,Chambron,Sauvage
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p. 12215 - 12221
(2007/10/03)
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- Applications of planar-chiral heterocycles in enantioselective catalysis: Cu(I)/bisazaferrocene-catalyzed asymmetric ring expansion of oxetanes to tetrahydrofurans
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A planar-chiral, C2-symmetric bisazaferrocene ligand is shown to control the stereochemistry of Cu(I)-catalyzed ring expansions of oxetanes to tetrahydrofurans.
- Lo, Michael M.-C.,Fu, Gregory C.
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p. 2621 - 2634
(2007/10/03)
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