- Preparation method of N-Boc-trans-cyclohexanediamine
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The invention discloses a preparation method of N-Boc-trans-cyclohexanediamine, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: dissolving trans-1, 4-cyclohexanediamine or (1S, 2S)-1, 2-cyclohexanediamine, tert-butyloxycarborylhydrazine and a copper catalyst in an organic solvent, and adding hydrogen peroxide to obtain the N-Boc-trans-cyclohexanediamine by a one-pot method. The method disclosed by the invention is simple to operate, and by controlling the equivalent weight of hydrogen peroxide, the temperature and the solvent concentration, the generation of a bis-t-butyloxycarboryl protecting group is effectively reduced, and the sufficient reaction of the raw material cyclohexanediamine is realized.
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Paragraph 0025-0030
(2021/10/13)
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- Directing the Solid-State Organization of Racemates via Structural Mutation and Solution-State Assembly Processes
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Chirality plays a central role in biomolecular recognition and pharmacological activity of drugs and can even lead to new functions such as spin filters. Although there have been significant advances in understanding and controlling the helical organizati
- Kulkarni, Chidambar,Berrocal, José Augusto,Lutz, Martin,Palmans, Anja R. A.,Meijer
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supporting information
p. 6302 - 6309
(2019/04/25)
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- Design, synthesis, and biological evaluation of radioiodinated benzo[d]imidazole-quinoline derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging
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Several malignant tumors and fibrotic diseases are associated with PDGFRβ overexpression and excessive signaling, making this receptor attractive for molecular targeting and imaging approaches. A series of benzo[d]imidazole-quinoline derivatives were designed and synthesized to develop radioiodinated compounds as PDGFRβ-specific imaging probes. The structure activity relationship (SAR) evaluation of the designed compounds was performed. Among them, 2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (5a) and 4-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (5d) exhibited a relatively high PDGFRβ-TK inhibitory potency, whereas iodinated 5a derivative 5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (8) exhibited a superior inhibitory potency as PDGFRβ inhibitor than iodinated 5d derivative 4-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (11). Furthermore, [125I]8 and [125I]11 were synthesized and evaluated for PDGFRβ radioligand ability, both in vitro and in vivo. Cellular uptake experiments showed that [125I]8 had a higher uptake in BxPC3-luc cells as PDGFRβ-positive cells than [125I]11. Incubation of [125I]8 after pretreatment of PDGFRβ ligands significantly reduced the uptake of [125I]8. In biodistribution experiments using tumor-bearing mice, [125I]8 accumulation in the tumor 1 h postinjection was higher than that of the benzo[d]imidazol-quinoline derivative [125I]IIQP, used in our previous research. These results indicate that [125I]8 could be a promising PDGFRβ imaging agent. Although its clinical application requires further structural modifications, the results obtained in this research may be useful for the development of PDGFRβ-specific radioligands.
- Effendi, Nurmaya,Mishiro, Kenji,Takarada, Takeshi,Yamada, Daisuke,Nishii, Ryuichi,Shiba, Kazuhiro,Kinuya, Seigo,Odani, Akira,Ogawa, Kazuma
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p. 383 - 393
(2019/01/04)
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- “Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts
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This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.
- Glasovac, Zoran,Kirin, Sre?ko I.,Kokan, Zoran,Opa?ak, Sa?a,Peri?, Berislav
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supporting information
p. 2115 - 2128
(2019/01/04)
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- Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins
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An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).
- Yan, Linjie,Huang, Guanxin,Wang, Haifeng,Xiong, Fangjun,Peng, Haihui,Chen, Fener
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supporting information
p. 99 - 103
(2018/01/17)
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- Solvent-induced reversal of enantioselectivity in the synthesis of succinimides by the addition of aldehydes to maleimides catalysed by carbamate-monoprotected 1,2-diamines
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A simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly disubstituted, to maleimides catalysed by chiral carbamate-monoprote
- Flores-Ferrndiz, Jess,Fiser, Bla,Gmez-Bengoa, Enrique,Chinchilla, Rafael
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supporting information
p. 1218 - 1225
(2015/03/04)
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- Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines
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Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeri
- Flores-Ferrándiz, Jesús,Chinchilla, Rafael
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p. 1091 - 1094
(2014/10/15)
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- Synthesis of novel macrocyclic tetraamides
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A simple and facile route has been described for the synthesis of macrocyclic tetraamides. This method is applicable for the preparation of a variety of macrocyclic tetraamides of various heteroatom substitutions.
- Mehta, Barun Kumar,Rambabu, Dandela,Raja, Guttikonda,Prasad,Fang, Jim-Min,Rao, Mandava Venkata Basaveswara
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p. 756 - 761
(2014/07/07)
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- Multivalent, high-relaxivity MRI contrast agents using rigid cysteine-reactive gadolinium complexes
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MRI contrast agents providing very high relaxivity values can be obtained through the attachment of multiple gadolinium(III) complexes to the interior surfaces of genome-free viral capsids. In previous studies, the contrast enhancement was predicted to de
- Garimella, Praveena D.,Datta, Ankona,Romanini, Dante W.,Raymond, Kenneth N.,Francis, Matthew B.
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supporting information; experimental part
p. 14704 - 14709
(2011/10/13)
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- Direct asymmetric aldol reaction catalyzed by C2-Symmetrical chiral primary amine organocatalysts
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Three novel C2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst.
- Zhu, Gong-Jian,Da, Chao-Shan,Jia, Ya-Ning,Ma, Xiao,Yi, Lei
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experimental part
p. 15 - 20
(2010/09/08)
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- An efficient chemoenzymatic method to prepare optically active primary-tertiary trans-cycloalkane-1,2-diamines
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Optically active trans-N-Boc-cyclopentane- and cyclohexane-1,2-diamines (7) were prepared by a chemoenzymatic method from the corresponding (±)-trans-N,N-diallylcycloalkane-1,2-diamine. These mono-carbamates 7 (ee=99%) were used as the starting materials
- Quijada, F. Javier,González-Sabín, Javier,Rebolledo, Francisca,Gotor, Vicente
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experimental part
p. 8028 - 8034
(2009/12/03)
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- Discovery of disubstituted cyclohexanes as a new class of CC chemokine receptor 2 antagonists
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We describe the design, synthesis, and evaluation of novel disubstituted cyclohexanes as potent CCR2 antagonists. Exploratory SAR studies led to the cis-disubstituted derivative 22, which displayed excellent binding affinity for CCR2 (binding IC50/s
- Cherney, Robert J.,Mo, Ruowei,Meyer, Dayton T.,Nelson, David J.,Lo, Yvonne C.,Yang, Gengjie,Scherle, Peggy A.,Mandlekar, Sandhya,Wasserman, Zelda R.,Jezak, Heather,Solomon, Kimberly A.,Tebben, Andrew J.,Carter, Percy H.,Decicco, Carl P.
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p. 721 - 724
(2008/09/18)
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- METAL CHELATORS AND METHODS OF THEIR USE
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Metal chelators of Formula (I) and Formula (II) are disclosed or a farmaceutically acceptable salt thereof. Also disclosed are metal chelator-targeting moiety complexes, metal chelator-targeting moiety-metal conjugates, kits, and methods of their preparation and use in diagnosis and/or treatment of diseases and conditions, including, inter alia, cancer and thrombosis.
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Page/Page column 24-25
(2008/06/13)
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- ETHYLENEDIAMINE DERIVATIVES
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The invention relates a compound represented by the formula (1):Q1-Q2-C(=O)-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 represent H or the like; Q1 represents an aromatic ring, heterocyclic ring or the like; Q2 represents a single bond, aromatic ring, heterocyclic ring or the like; Q3 represents a group or the like, Q4 represents an aromatic ring, heterocyclic ring or the like; and T1 represents -CO- or -SO2-, and a medicine which comprises the compound and is useful for thrombosis and embolism.
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- Heterocycle derivatives and drugs
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There is provided an excellent novel analgesic having an analgesic effect which is effective widely against a pain including a chronic pain or an allodynia accompanied with herpes zoster by acting on a nociceptin receptor. The present invention relates to a compound represented by the following formula: or a salt thereof. In the formula, X and Y are same or different and each represents a nitrogen atom or CH; R1 represents a hydrogen atom or alkyl and the like; A1 and A2 are same or different and each represents a single bond or a divalent aliphatic hydrocarbon group; Q represents a single bond, cycloalkylene group, phenylene group or divalent heterocyclic group; R2A, R2B, R2C and R2D are same or different and each represents a hydrogen atom, alkyl or phenyl; E represents a ethenylene group or —NRCO— (in which R is hydrogen or alkyl) and the like; R3 represents a phenyl group or a heterocyclic group; R4 and R5 are same or different and each represents a hydrogen atom, alkyl, alkoxy, aralkyloxy, halogen, nitro, hydroxy, alkoxycarbonyl, —NR6R7 (in which R6 and R7 are same or different and each represents a hydrogen atom or alkyl) and the like.
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- Compositions and methods for enhancing drug delivery across and into ocular tissues
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This invention provides compositions and methods for enhancing delivery of drugs and other agents across epithelial tissues, including into and across ocular tissues and the like. The compositions and methods are also useful for delivery across endothelial tissues, including the blood brain barrier. The compositions and methods employ a delivery enhancing transporter that has sufficient guanidino or amidino sidechain moieties to enhance delivery of a compound conjugated to the reagent across one or more layers of the tissue, compared to the non-conjugated compound. The delivery-enhancing polymers include, for example, poly-arginine molecules that are preferably between about 6 and 25 residues in length.
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- Compositions and methods for enhancing drug delivery across and into epithelial tissues
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This invention provides compositions and methods for enhancing delivery of drugs and other agents across epithelial tissues, including the skin, gastrointestinal tract, pulmonary epithelium, ocular tissues and the like. The compositions and methods are also useful for delivery across endothelial tissues, including the blood brain barrier. The compositions and methods employ a delivery enhancing transporter that has sufficient guanidino or amidino sidechain moieties to enhance delivery of a compound conjugated to the reagent across one or more layers of the tissue, compared to the non-conjugated compound. The delivery-enhancing polymers include, for example, poly-arginine molecules that are preferably between about 6 and 25 residues in length.
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- Approaches towards the enantioselective recognition of anionic guest species using chiral receptors based on rhenium(I) and ruthenium(II) with amide bipyridine ligands
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The syntheses of chiral anion receptors based on rhenium(I) and ruthenium(II) with amide bipyridine ligands are reported. The rhenium(I) hosts were prepared in moderate to high yields by co-ordinating chiral bipyridine ligands to a Re(CO)3Br centre. The ruthenium(II) receptors were synthesised via the chiral building blocks Λ- and Δ-[Ru(bpy)2-(py)2]2+ or by chromatographic resolution on a SP Sephadex C-25 cation exchanger. Chiral purity was determined by 1H NMR and circular dichroism spectroscopy and lanthanide shift experiments. 1H NMR titration studies showed that these receptors bind chiral carboxylate anions in DMSO-d6, although significant chiral discrimination was not observed.
- Uppadine,Keene,Beer
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p. 2188 - 2198
(2007/10/03)
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- Synthesis of piperazinones and benzopiperazinones from 1,2-diamines and organoboronic acids
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Alkenyl, aryl and heteroaryl boronic acids react with 1,2-diamines and glyoxylic acid to give directly in one step the corresponding piperazinones (2-oxopiperazines). Similarly, the use of monoprotected 1,2-phenylenediamine leads to benzopiperazinones (1,2,3,4-tetrahydroquinoxalin-2-ones). (C) 2000 Elsevier Science Ltd.
- Petasis,Patel
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p. 9607 - 9611
(2007/10/03)
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- Chiral peptide nucleic acid monomers and oligomers
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A novel class of peptide nucleic acid monomers are synthesized having chirality in the backbone. Peptide nucleic acid oligomers are synthesized to incorporate these chiral monomers.
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- Peptide nucleic acids with a conformationally constrained chiral cyclohexyl-derived backbone
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Peptide nucleic acid (PNA) is an achiral nucleic acid mimic with a backbone consisting of partly flexible aminoethyl glycine units. By replacing the aminoethyl portion of the backbone by an amino cyclohexyl moiety, either in the (S,S) or the (R,R) configu
- Lagriffoule, Pierre,Wittung, Pernilla,Eriksson, Magdalena,Jensen, Kristine Kilsa,Norden, Bengt,Buchardt, Ole,Nielsen, Peter E.
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p. 912 - 919
(2007/10/03)
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