10027-07-3Relevant articles and documents
Behavior of Ruthenium Trisbipyridine-Anthraquinone Conjugates Connected with Alkyl Spacers in Homogeneous and Microheterogeneous Media
Otsuki, Joe,Ogawa, Hiroyuki,Okuda, Naotoshi,Araki, Koji,Seno, Manabu
, p. 2077 - 2084 (1997)
A series of mononuclear Ru trisbypiridine complexes connected to an anthraquinone unit by a flexible alkyl chain of varying lengths and a bolaamphiphilic dinuclear ruthenium complex bearing an anthraquinone unit in the middle of alkyl chain spacers were synthesized. Their conformational preference in CH3CN and in dihexadecyl phosphate vesicles was probed by utilizing the intramolecular electron-transfer quenching of the metal-to-ligand charge-transfer excited state of the Ru center by the appended quinone moiety. The length of the alkyl chain spacer had little effect on the quenching efficiency in either medium. A marked difference in the quenching behavior was observed only in the case of the dinuclear Ru complex in vesicles. These results indicate that the bolaamphiphilic structure is necessary and effective for the set of immobilized molecules to take a stretched conformation spanning a bilayer membrane.
Use of acylphosphonates for the synthesis of α-chlorinated carboxylic and α,α′-dichloro dicarboxylic acids and their derivatives
Stevens, Christian V,Vanderhoydonck, Bart
, p. 4793 - 4800 (2001)
α-Chloro acylphosphonates and α,α′-dichloro bisacylphosphonates were prepared in situ by chlorination of acylphosphonates and bisacylphosphonates, respectively, using sulfuryl chloride. Subsequently, they were cleaved to the corresponding α-chlorinated or α,α′-dichlorinated (di)carboxylic acids with a hydrogen peroxide-sodium bicarbonate system. Performing the cleavage with an alcohol or an amine yielded the corresponding α-chlorinated esters and α-chlorinated amides, respectively.
Homobivalent ligands of the atypical antipsychotic clozapine: Design, synthesis, and pharmacological evaluation
McRobb, Fiona M.,Crosby, Ian T.,Yuriev, Elizabeth,Lane, J. Robert,Capuano, Ben
, p. 1622 - 1634 (2012)
To date all typical and atypical antipsychotics target the dopamine D 2 receptor. Clozapine represents the best-characterized atypical antipsychotic, although it displays only moderate (submicromolar) affinity for the dopamine D2 receptor. Herein, we present the design, synthesis, and pharmacological evaluation of three series of homobivalent ligands of clozapine, differing in the length and nature of the spacer and the point of attachment to the pharmacophore. Attachment of the spacer at the N4′ position of clozapine yielded a series of homobivalent ligands that displayed spacer-length-dependent gains in affinity and activity for the dopamine D 2 receptor. The 16 and 18 atom spacer bivalent ligands were the highlight compounds, displaying marked low nanomolar receptor binding affinity (1.41 and 1.35 nM, respectively) and functional activity (23 and 44 nM), which correspond to significant gains in affinity (75- and 79-fold) and activity (9- and 5-fold) relative to the original pharmacophore, clozapine. As such these ligands represent useful tools with which to investigate dopamine receptor dimerization and the atypical nature of clozapine.
Synthesis of α,ω-Diketodiesters from Betulin
Ishmuratov, G. Yu.,Sayakhov, R. R.,Talipov, R. F.,Vydrina, V. A.,Yakovleva, M. P.,Zileeva, Z. R.
, p. 706 - 711 (2021)
A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. α,ω-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydroxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized α,ω-diketodiesters was moderately active in vitro against A-549 lung carcinoma.
A new class of star-shaped cholesteric liquid crystal containing a 1,3,5-trihydroxybenzene unit as a core
Yao, Dan-Shu,Zhang, Bao-Yan,Zhang, Wei-Wei,Tian, Mei
, p. 83 - 89 (2008)
A new class of star-shaped cholesteric liquid crystals were designed and synthesized, which used 1,3,5-trihydroxybenzene unit as a core and ω-cholesteric alkyl diacid monoester as mesogenic arm. Their chemical structures were confirmed by element analyses, FT-IR, and 1H NMR. The mesomorphic properties and thermal stability were investigated by differential scanning calorimetry, thermogravimetric analysis, polarizing optical microscopy, and X-ray diffraction measurements. The experimental results demonstrated that the mesogenic arm structures strongly affected the phase behavior. 4a did not show any liquid crystallinity, while 4b, 4c and 4d revealed reversible cholesteric phase transition. As the intermedius alkyl chain of the star-shaped compounds lengthened (from n = 2 to n = 8), their melting points decreased but mesomorphic temperature ranges increased. Focal conic texture, one of cholesteric phase can be observed in the liquid crystalline state.
Synthesis of novel α,ω-type 1-glucosamide and 1-galactosamide bolaamphiphiles
Masuda, Mitsutoshi,Shimizu, Toshimi
, p. 405 - 416 (1998)
A new family of bolaamphiphiles in which two glucosylamine or galactosylamine moieties are linked via a β-N-glycosdic bond to an α,ω-dicarboxylic acid has been described. The 1-D-glucosamide and 1-D-galactosamide bolaamphiphiles were obtained in good yield by the condensation of the dicarboxylic acid dichloride with the corresponding 1-aldopyranosylamine.
Symmetric dimeric adamantanes for exploring the structure of two viroporins: Influenza virus M2 and hepatitis C virus p7
Mandour, Yasmine M.,Breitinger, Ulrike,Ma, Chunlong,Wang, Jun,Boeckler, Frank M.,Breitinger, Hans-Georg,Zlotos, Darius P.
, p. 1019 - 1031 (2018)
Background: Adamantane-based compounds have been identified to interfere with the ion-channel activity of viroporins and thereby inhibit viral infection. To better understand the difference in the inhibition mechanism of viroporins, we synthesized symmetric dimeric adamantane analogs of various alkyl-spacer lengths. Methods: Symmetric dimeric adamantane derivatives were synthesized where two amantadine or rimantadine molecules were linked by various alkyl-spacers. The inhibitory activity of the compounds was studied on two viroporins: the influenza virus M2 protein, expressed in Xenopus oocytes, using the two-electrode voltage-clamp technique, and the hepatitis C virus (HCV) p7 channels for five different genotypes (1a, 1b, 2a, 3a, and 4a) expressed in HEK293 cells using whole-cell patch-clamp recording techniques. Results: Upon testing on M2 protein, dimeric compounds showed significantly lower inhibitory activity relative to the monomeric amantadine. The lack of channel blockage of the dimeric amantadine and rimantadine analogs against M2 wild type and M2-S31N mutant was consistent with previously proposed drug-binding mechanisms and further confirmed that the pore-binding model is the pharmacologically relevant drug-binding model. On the other hand, these dimers showed similar potency to their respective monomeric analogs when tested on p7 protein in HCV genotypes 1a, 1b, and 4a while being 700-fold and 150-fold more potent than amantadine in genotypes 2a and 3a, respectively. An amino group appears to be important for inhibiting the ion-channel activity of p7 protein in genotype 2a, while its importance was minimal in all other genotypes. Conclusion: Symmetric dimeric adamantanes can be considered a prospective class of p7 inhibitors that are able to address the differences in adamantane sensitivity among the various genotypes of HCV.
Investigation of novel ropinirole analogues: Synthesis, pharmacological evaluation and computational analysis of dopamine D2 receptor functionalized congeners and homobivalent ligands
J?rg, Manuela,Kaczor, Agnieszka A.,Mak, Frankie S.,Lee, Kiew Ching K.,Poso, Antti,Miller, Neil D.,Scammells, Peter J.,Capuano, Ben
, p. 891 - 898 (2014)
Herein, we report the development of novel functionalized congeners of ropinirole toward the design of pharmacological tools to probe structural requirements at the dopamine D2 receptor. Subsequently, we have used the functionalized amine congener 11 and synthesized and pharmacologically evaluated a series of homobivalent ligands of ropinirole with designated spacer lengths ranging from 14 to 30 atoms. The most potent homobivalent ligands (22-, 26- and 30-atom spacers) showed approximately 20- to 80-fold greater potency (EC50 = 3.9, 6.2 and 14 nM, respectively) than ropinirole (304 nM) in a [35S]GTPγS functional assay. Molecular modeling studies suggest that the observed increase in potency of the homobivalent ligands is possibly due to a bitopic binding mode involving the orthosteric site and an allosteric interaction at the dopamine D2 receptor protomer rather than bridging interactions at two orthosteric sites across a dopamine D 2 receptor dimer. This research has the potential to advance the development of structurally related bitopic ligands, biomarkers such as radioligands and fluorescently labeled probes, and furnish new homo- and heterobivalent ligands towards a better understanding of the dopamine D 2 receptor and potential novel treatment for Parkinson's disease.
Electrocatalytic debromination of open-chain and cyclic dibromides in ionic liquids with cobalt(II)salen complex as mediator
Shen, Yi,Inagi, Shinsuke,Atobe, Mahito,Fuchigami, Toshio
, p. 89 - 99 (2013)
The electrocatalytic reduction of open-chain and cyclic dibromides in ionic liquids, mediated by cobalt(II)salen, was investigated. Macro-scale constant-potential electrolysis in an undivided cell gave the corresponding debrominated products in moderate to good yields. The workup process after electrolysis proved to be much simpler in the ionic liquid than that in organic solvents. The possibility of reuse of the ionic liquid was demonstrated.
A SUNSCREEN FORMULATION
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Paragraph 00129-00132, (2021/03/19)
Provided herein is synthesis of new classes of sunscreen agents, the usage of such sunscreen agents to prepare sunscreen formulation materials aiming at reduction of sunscreen agents' skin penetration. The whole purpose is to improve the biosafety of sunscreen products via novel sunscreen materials and formulation technology to reduce or to eliminate skin penetration of sunscreen agents. The technology can be applied to cosmetics, pharmaceutical or insects' repellent products.
