821-06-7Relevant articles and documents
Metathesis Cascade-Triggered Depolymerization of Enyne Self-Immolative Polymers**
Giardino, Gavin J.,Niu, Jia,Yuan, Jingsong
supporting information, p. 24800 - 24805 (2021/10/07)
A novel class of enyne self-immolative polymers (SIPs) capable of metathesis cascade-triggered depolymerization is reported. Studies on model compounds established 1,6-enyne structures for efficient metathesis cascade reactions. SIPs incorporating the optimized 1,6-enyne motif were prepared via both polycondensation and iterative exponential growth approaches. These SIPs demonstrated excellent stability in strong acid, base, nucleophiles, or at elevated temperatures, and can undergo efficient and complete depolymerization once triggered by a metathesis catalyst. Further studies revealed that introducing a terminal alkene to the chain end of the enyne SIPs improved the depolymerization efficiency, and established their potential as stimuli-responsive materials.
D3 RECEPTOR AGONIST COMPOUNDS; METHODS OF PREPARATION; INTERMEDIATES THEREOF; AND METHODS OF USE THEREOF
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Paragraph 0083; 0118, (2020/10/21)
Disclosed herein are novel compounds including dopamine D3 receptor agonists, compositions thereof, methods of use thereof, and processes of synthesizing the same. Further disclosed are D3R selective agonist compounds, specifically bitopic ligands comprising chirality.
The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D3 Receptor (D3R) Selective Agonists
Battiti, Francisco O.,Cemaj, Sophie L.,Guerrero, Adrian M.,Shaik, Anver Basha,Lam, Jenny,Rais, Rana,Slusher, Barbara S.,Deschamps, Jeffery R.,Imler, Greg H.,Newman, Amy Hauck,Bonifazi, Alessandro
, p. 6287 - 6314 (2019/08/02)
Because of the large degree of homology among dopamine D2-like receptors, discovering ligands capable of discriminating between the D2, D3, and D4 receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chemical modification of the D3 preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D3R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D3R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D3R binding selectivities than the reference compounds. Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation.
Axinellamines as broad-spectrum antibacterial agents: Scalable synthesis and biology
Rodriguez, Rodrigo A.,Barrios Steed, Danielle,Kawamata, Yu,Su, Shun,Smith, Peter A.,Steed, Tyler C.,Romesberg, Floyd E.,Baran, Phil S.
supporting information, p. 15403 - 15413 (2015/01/09)
Antibiotic-resistant bacteria present an ongoing challenge to both chemists and biologists as they seek novel compounds and modes of action to out-maneuver continually evolving resistance pathways, especially against Gram-negative strains. The dimeric pyrrole-imidazole alkaloids represent a unique marine natural product class with diverse primary biological activity and chemical architecture. This full account traces the strategy used to develop a second-generation route to key spirocycle 9, culminating in a practical synthesis of the axinellamines and enabling their discovery as broad-spectrum antibacterial agents, with promising activity against both Gram-positive and Gram-negative bacteria. While their detailed mode of antibacterial action remains unclear, the axinellamines appear to cause secondary membrane destabilization and impart an aberrant cellular morphology consistent with the inhibition of normal septum formation. This study serves as a rare example of a natural product initially reported to be devoid of biological activity surfacing as an active antibacterial agent with an intriguing mode of action.
Continuous flow olefin metathesis using a multijet oscillating disk reactor as the reaction platform
Bjorsvik, Hans-Ren,Liguori, Lucia
, p. 1509 - 1515 (2015/02/19)
The multijet oscillating disk (MJOD) flow reactor is a relatively new technology for continuous flow synthesis. This technology is still under investigation as an all-round platform for flow synthesis. In this article, findings are disclosed from a project where a MJOD flow reactor rig (reactor volume of ≈50 mL) was investigated as the reaction platform for ring closing metathesis and cross (self) metathesis reaction, using reaction mixture volumes down to only ≈5 mL. The Hoveyda-Grubbs second-generation catalyst was used without an inert atmosphere. The results of the flow synthesis provided excellent selectivity and high yield. For comparison purposes, the syntheses conducted in the MJOD reactor were compared with similar literature experiments performed with other flow technologies and batch conditions.
C10 Dialdehyde, Synthetic Method Thereof, and Synthetic Method of Beta-Carotene Using the Same
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Page/Page column 6, (2008/12/04)
The novel intermediate compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the practical synthetic process for preparing β-carotene by the use of the above novel compound are disclosed. The synthesis of β-carotene is characterized by the double elimination reactions of the C40 compound containing both the benzenesulfonyl group and the group X (either halogen or ether), which can be prepared by the coupling reaction of the novel C10 dialdehyde with two equivalents of the C15 allylic sulfone, followed by the functional group transformation of the resulting C40 diol either to the corresponding halide or to the ether, to produce the fully conjugated polyene chain.
ClO DIALDEHYDE, SYNTHETIC METHOD THEREOF, AND SYNTHETIC METHOD OF BETA-CAROTENE USING THE SAME
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Page/Page column 9-10, (2010/10/20)
The novel intermediate compound which can be efficiently utilized in the synthesis of carotenoid compounds based on the sulfone chemistry, the preparation method of the same, and the practical synthetic process for preparing β-carotene by the use of the above novel compound are disclosed. The synthesis of β-carotene is characterized by the double elimination reactions of the C40 compound containing both the benzenesulfonyl group and the group X (either halogen or ether), which can be prepared by the coupling reaction of the novel C10 dialdehyde with two equivalents of the C15 allylic sulfone, followed by the functional group transformation of the resulting C40 diol either to the corresponding halide or to the ether, to produce the fully conjugated polyene chain.
Palladium(0)-catalyzed allylation of highly acidic and non-nucleophilic arenesulfonamides, sulfamide, and cyanamide. II. Formation of medium and large heterocycles
Cerezo, Silvia,Cortes, Jordi,Lopez-Romero, Juan-Manuel,Moreno-Manas, Marcial,Parella, Teodor,Pleixats, Roser,Roglans, Anna
, p. 14885 - 14904 (2007/10/03)
Arenesulfonamides 10, cyanamide 29, and sulfamide 32 react with allylic bis-carbonates 8 (Z and E) and 9 under Pd(0)-catalysis to afford medium and large unsaturated heterocycles instead of three and/or five-membered ring compounds. Stable 15-membered palladium-containing rings were also isolated from arenesulfonamides and 8, with three trans olefinic systems coordinated to the metal. NMR and MALDI-TOF MS experiments were used for structure elucidations. Suitable hydrogenation conditions to give the saturated macrocycles have been found.
Azole compounds and fungicides containing these compounds
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, (2008/06/13)
Azole compounds of the formula STR1 where V is oxygen or sulfur, X is hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, phenyl or phenoxy, m is an integer from 1 to 5, W is an olefin group which is unsubstituted or substituted, or is alkynyl, Z is CH or N, and Y is C=O or CR3 OR4, where R3 is hydrogen, alkyl, alkenyl or alkynyl, and R4 is hydrogen, alkyl, alkenyl, alkynyl or alkanoyl, and their plant-tolerated addition salts with acids and metal complexes, and fungicides which contain these compounds.
A reinvestigation of the vapor phase bromination of 2-bromobutane
Tanner, Dennis D.,Ruo, Tomoki C. S.,Kosugi, Yoshio,Potter, Alan
, p. 2310 - 2316 (2007/10/02)
The soltuion phase photobromination of 2-bromobutane yields 2,2-dibromobutane, meso-2,3-dibromobutane, dl-2,3-dibromo-dibromobutane, small amounts of 1,2-dibromobutane, and 2,2,3-tribromobutane.However, in the corresponding vapor phase bromination these products appear along with other polybrominated products.The yield of these polybromides increases with temperature.The increase in yield of the polyhalogenated materials is rationalized by considering the thermal instabilty of the β-bromoalkyl radical, which eliminates a bromine atom to form the corresponding alkene.It is demonstrated that in the vapor phase allylic bromination competes succesfully with bromine addition.Reaction schemes are suggested to explain the formation of polybromides.An explanation is also offered for the dicrepancy between these results and those of previously reported vapor phase work.
