- Understanding the Structure–Polymerization Thermodynamics Relationships of Fused-Ring Cyclooctenes for Developing Chemically Recyclable Polymers
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Polymers that can be chemically recycled to their constituent monomers offer a promising solution to address the challenges in plastics sustainability through a circular use of materials. The design and development of monomers for next-generation chemical
- Sathe, Devavrat,Wang, Junpeng,Zhou, Junfeng
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p. 928 - 934
(2022/01/19)
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- Hydrogenated Poly(Dewar benzene): A Compact Cyclic Olefin Polymer with Enhanced Thermomechanical Properties
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Dihydro Dewar benzene(bicyclo[2.2.0]hex-2-ene) was synthesized and polymerized using the Grubbs third generation catalyst. The corresponding ring-opening metathesis polymerization proceeded in a controlled manner, as determined by a linear relationship between the molecular weight of the polymer produced and the monomer-To-catalyst feed ratio as well as an ability to extend polymer chains through exposure to an additional monomer. Subsequent treatment with tosylhydrazide afforded the corresponding hydrogenated derivative. The hydrogenated polymer was found to exhibit high melting and decomposition temperatures as well as a relatively high Young's modulus when compared to other polyolefins [e.g., hydrogenated poly(norbornene) and poly(ethylene)]. The enhanced thermal and mechanical properties were found to originate from a relatively low phase transition entropy combined with high polymer crystallinity, features that were attributed to restricted bond rotation within the repeating units of the hydrogenated polymer.
- Bielawski, Christopher W.,Lee, Stanfield Y.,Seo, Jinwon
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- MACROCYCLIC SPIROETHERS AS MCL-1 INHIBITORS
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Provided are compounds represented by Formula (I-A) and the pharmaceutically acceptable salts and solvates thereof, wherein R8, R9a, R9b, R9c, R9d, X, Y, Z, Z1, W, and (aa) are as defined as set forth in the specification. Provided are also compounds of Formula (I-A) for use to treat a condition or disorder responsive to Mcl-1 inhibition such as cancer.
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- ALPHA-HYDROXY PHENYLACETIC ACID PHARMACOPHORE OR BIOISOSTERE MCL-1 PROTEIN ANTAGONISTS
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Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, or a stereoisomer thereof; and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 74-75
(2019/10/01)
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- MACROCYCLIC CHLORINE SUBSTITUTED INDOLE DERIVATIVES
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The present invention relates to macrocyclic indole derivatives of general formula (I) : (I), in which R1, R2, R3, R4, R5, R6, A and L are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active 10 ingredients.
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Page/Page column 355
(2019/06/13)
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- MACROCYCLIC CHLORINE SUBSTITUTED INDOLE DERIVATIVES
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The present invention relates to macrocyclic indole derivatives of general formula (I) : in which R1, R2, R3, R4, R5, R6, A and L are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients.
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Page/Page column 286
(2019/06/09)
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- COMPOUNDS THAT INHIBIT MCL-1 PROTEIN
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Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (I), or a stereoisomer thereof; and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 793
(2018/10/25)
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- LADDERANE LIPID COMPOUNDS AND LIPOSOMES AND METHODS OF PREPARING AND USING THE SAME
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Methods for preparing a variety of ladderane precursors, ladderane compounds and ladderane lipids are provided. Also provided are methods of preparing a liposome from the ladderane lipids disclosed herein, and compositions thereof. Aspects of the invention include encapsulated one or more cargo moieties in the liposome or compositions thereof and use of the subject liposome compositions as vehicles in drug delivery, imaging, diagnostics and other medical applications. Aspects of the methods disclosed herein include administering a liposomal composition comprising a pharmaceutical agent to a subject under conditions sufficient to deliver the composition to a site of interest in the subject, and release the pharmaceutical agent from the liposomal composition.
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Page/Page column 51; 52
(2018/03/25)
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- Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds
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Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.
- Wang, Yaxin,Hu, Xiafei,Morales-Rivera, Cristian A.,Li, Guo-Xing,Huang, Xin,He, Gang,Liu, Peng,Chen, Gong
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supporting information
p. 9678 - 9684
(2018/07/21)
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- COMPOUNDS THAT INHIBIT MCL-1 PROTEIN
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Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 69; 70
(2017/09/15)
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- TETRAHYDRONAPHTHALENE DERIVATIVES THAT INHIBIT MCL-1 PROTEIN
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Provided herein are myeloid cell leukemia 1 protein (Mcl-1) inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula I, (I) and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing the compounds. The compounds and compositions provided herein may be used, for example, in the treatment of diseases or conditions, such as cancer.
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Page/Page column 74; 75
(2016/03/22)
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- Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid
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Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.
- Mercer, Jaron A. M.,Cohen, Carolyn M.,Shuken, Steven R.,Wagner, Anna M.,Smith, Myles W.,Moss, Frank R.,Smith, Matthew D.,Vahala, Riku,Gonzalez-Martinez, Alejandro,Boxer, Steven G.,Burns, Noah Z.
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supporting information
p. 15845 - 15848
(2016/12/23)
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- A Stereochemical Study of the Thermolysis of cis-anti- and trans-1,2-Dimethyl-cis-3,4-dideuteriocyclobutane
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The stereochemistry of the fragmentation and isomerization of cis-anti- and trans-1,2-dimethyl-cis-3,4-dideuteriocyclobutane at 510 deg C is reported.The cis-anti-cis isomer undergoes fragmentation to yield cis/trans-propene-d1 (1.5/1, major pathway), cis/trans-2-butene (1.4/1), and cis/trans-ethylene-d2 (1/1, minor pathway).Recovered cis-1,2-dimethylcyclobutane-d2 containing approximately 40percent of the double rotation product relative to the product of single methyl rotation, trans-1,2-dimethylcyclobutane-d2.The trans isomer behaves similarly, yielding cis/trans-propene-d1 (1/1, major pathway), cis/trans-2-butene (1/5), and cis/trans-ethylene-d2 (1/1, minor pathway).Recovered cis-1,2-dimethylcyclobutane-d2 from thermolysis of the trans isomer consists mainly of equal amounts of cis-anti-cis- and cis-syn-cis-1m2-dimethylcyclobutane-d2 as analyzed by NMR.On the basis of product composition, the thermal chemistry of this system can be explained as proceeding through 2,5-hexanediyl (major pathway) and 3-methyl-1,4-pentanediyl (minor pathway).On the basis of the observed stereochemistry, it can be concluded that the lifetimes of both 2,5-hexanediyl and 3-methyl-1,4-pentanediyl are similar and of the same order as bond rotations at a radical center.This suggests that the gauche to trans conformational changes involving carbon-carbon bond rotation at carbon 2 and 3 of 1,4-diyls may not be competitive with fragmentation.
- Wang, Yen-Seine,Chickos, James S.
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p. 4776 - 4781
(2007/10/02)
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- Enzymes in Organic Synthesis. 24. Preparations of Enantiomerically Pure Chiral Lactones via Stereospecific Horse Liver Alcohol Dehydrogenase Catalyzed Oxidations of Monocyclic Meso Diols
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Preparative-scale horse liver alcohol dehydrogenase catalyzed oxidation of monocyclic meso diols provides a direct and convenient one-step route to a broad range of chiral γ-lactones of value as synthons in asymmetric synthesis.The general applicability of the method is demonstrated by oxidations of cis-1,2-bis(hydroxymethyl) substrates of the cyclohexyl, cyclohexenyl, cyclopentyl, cyclobutyl, cyclopropyl, and dimethylcyclopropyl series.For each diol, oxidation of the hydroxymethyl group attached to the S chiral center occurs exclusively, and the pure γ-lactone products are isolated in high (68-90percent) yields and of 100percent ee.In contrast, the enzyme does not exhibit significant enantiomeric selectivity in its catalysis of oxidations of the corresponding racemic trans diols.The stereospecificities observed, or lack thereof, are as predicted by the active-site model.
- Jakovac, Ignac J.,Goodbrand, H. Bruce,Lok, Kar P.,Jones, J. Bryan
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p. 4659 - 4665
(2007/10/02)
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- Reactions of α-Halotetrahydrothiophene 1,1-Dioxides with Strong Bases
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This article describes the halogenated sulfones 2, 3, 7, 11, 16 and 18 obtained from the hitherto unknown intermediates 4, 5, 6 and 8, 9, 10 and from 14, 15.An account is given of Ramberg-Baecklund-type reactions undergone by the α-halogenated cyclic sulfones 2a and 7 with bases at high temperature.
- Neidlein, Richard,Doerr, Henning
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p. 1540 - 1548
(2007/10/02)
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