6947-15-5Relevant academic research and scientific papers
Towards Enediyne Libraries: Cyclic Enediynes via an Intramolecular Carbenoid Coupling Protocol
Jones, Graham B.,Huber, Robert S.,Mathews, Jude E.
, p. 1791 - 1792 (1995)
Functionalised bioactive enediynes can be produced via an intramolecular carbenoid coupling of bis-prop-2-ynylic halides, and elaborated into useful synthons via their dicobalt hexacarbonyl complexes.
Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation
Emmetiere, Fabien,Grenning, Alexander J.
, p. 3077 - 3085 (2020/08/10)
Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process invol
NON-LYSOSOMAL GLUCOSYLCERAMIDASE INHIBITORS AND USES THEREOF
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Paragraph 00196, (2020/12/01)
The invention provides compounds for inhibiting glucosylceramidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds.
Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 4992 - 4997 (2019/03/13)
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
Probing Intramolecular Electron Transfer in Redox Tag Processes
Maeta, Naoya,Kamiya, Hidehiro,Okada, Yohei
supporting information, p. 8519 - 8522 (2019/11/20)
Herein, we show that redox tag-guided intermolecular formal [2 + 2] cycloaddition can be used as a probe to investigate intramolecular single-electron transfer (SET) mechanisms. The efficacy of intramolecular SET can be evaluated in association with concomitant carbon-carbon bond formation and/or cleavage, leading to cycloaddition or cross-metathesis. Experimental and theoretical results suggest that the intramolecular SET is under both thermodynamic and kinetic control and can also occur through bonds, not only through space.
Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow
Chen, Yiding,Leonardi, Marco,Dingwall, Paul,Labes, Ricardo,Pasau, Patrick,Blakemore, David C.,Ley, Steven V.
, p. 15558 - 15568 (2019/01/04)
Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.
Synthesis and Structure-Activity Relationships of Triazaspirodecanone Derivatives as Nociceptin/Orphanin FQ Receptor Ligands
Corrado, Sandra,Battisti, Umberto M.,Sorbi, Claudia,Tait, Annalisa,Malfacini, Davide,Camarda, Valeria,Calò, Girolamo,Brasili, Livio
, p. 447 - 458 (2015/02/19)
Several spiroxatrine derivatives were synthesized and evaluated as potential NOP receptor ligands. Structural modifications of the 1,4-benzodioxane moiety of spiroxatrine have been the focus of this research project. The structure-activity relationships that emerged indicate that the presence of an H-bond donor group (hydroxyl group) is more favorable for NOP activity when it is positioned α with respect to the CH2 linked to the 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one portion. Moreover, cis diastereoisomers of the hydroxyl derivatives4 and 22 show a moderately higher degree of stereoselectivity than trans isomers. In particular, the spiropiperidine derivative cis-4 has submicromolar agonistic activity, and it will be the reference compound for the design and synthesis of new NOP agonists.
Synthesis of alcohols via a rhodium-catalyzed hydroformylation-reduction sequence using tertiary bidentate amine ligands
Cheung, Lawrence L. W.,Vasapollo, Giuseppe,Alper, Howard
supporting information; experimental part, p. 2019 - 2022 (2012/09/22)
The synthesis of alcohols from aromatic olefins is described using a rhodium-catalyzed hydroformylation-reduction sequence with the assistance of a tertiary diamine ligand. The alcohols are produced in excellent branched to linear ratios and in good to excellent isolated yields. In all cases no aldehyde product, from hydroformylation, or alkyl product, from olefin reduction, was detected. Copyright
Cytochrome P450BM-3 reduces aldehydes to alcohols through a direct hydride transfer
Kaspera, Rüdiger,Sahele, Tariku,Lakatos, Kyle,Totah, Rheem A.
experimental part, p. 464 - 468 (2012/07/27)
Cytochrome P450BM-3 catalyzed the reduction of lipophilic aldehydes to alcohols efficiently. A kcat of ～25min-1 was obtained for the reduction of methoxy benzaldehyde with wild type P450BM-3 protein which was higher than in the isolated reductase domain (BMR) alone and increased in specific P450-domain variants. The reduction was caused by a direct hydride transfer from preferentially R-NADP2H to the carbonyl moiety of the substrate. Weak substrate-P450-binding of the aldehyde, turnover with the reductase domain alone, a deuterium incorporation in the product from NADP2H but not D2O, and no inhibition by imidazole suggests the reductase domain of P450BM-3 as the potential catalytic site. However, increased aldehyde reduction by P450 domain variants (P450BM-3 F87A T268A) may involve allosteric or redox mechanistic interactions between heme and reductase domains. This is a novel reduction of aldehydes by P450BM-3 involving a direct hydride transfer and could have implications for the metabolism of endogenous substrates or xenobiotics.
Synthesis and protein degradation capacity of photoactivated enediynes
Fouad, Farid S.,Wright, Justin M.,Plourde II, Gary,Purohit, Ajay D.,Wyatt, Justin K.,El-Shafey, Ahmed,Hynd, George,Crasto, Curtis F.,Lin, Yiqing,Jones, Graham B.
, p. 9789 - 9797 (2007/10/03)
The viability of proteins as targets of thermally and photoactivated enediynes has been confirmed at the molecular level. Model studies using a labeled substrate confirmed the efficacy of atom transfer from diyl radicals produced from enediynes to form captodatively stabilized carbon centered aminoacyl radicals, which then undergo either fragmentation or dimerization. To exploit this finding, a family of enediynes was developed using an intramolecular coupling strategy. Derivatives were prepared and used to target specific proteins, showing good correlation between affinity and photoinduced protein degrading activity. The findings have potential applications in the design of artificial chemical proteases and add to our understanding of the mechanism of action of the clinically important enediyne antitumor antibiotics.
