51309-22-9Relevant academic research and scientific papers
A concise, protection-free and divergent approach for the enantioselective syntheses of two pheromonal epoxide components of the fall webworm moth and other species
Du, Yu,Zheng, Jian-Feng,Wang, Zhi-Gang,Jiang, Li-Jiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
, p. 4619 - 4622 (2010)
(Figure presented) On the basis of Zhous modified Sharpless asymmetric epoxidation, sequential coupling reactions, and a divergent strategy, the protection-free syntheses of two main pheromonal components 1 and 5, found in the fall webworm moth, Hyphantria cunea, and other species have been accomplished in 10 steps (for two compounds). The overall yields are 31% for 1, 28% for 5, and 25% for both 1 and 5, respectively. The ee values of the final products 1 and 5 are at least 99%.
Method for synthesizing sex pheromone of hyphantria cunea
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Paragraph 0048-0049, (2021/04/17)
The invention relates to the technical field of hyphantria cunea prevention and treatment, in particular to a synthetic method for synthesizing sex pheromone of hyphantria cunea. According to a traditional method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene by using propargyl alcohol as a starting material in the traditional technology, various side reactions are liable to occur during a sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by using trifluoromethanesulfonic anhydride. In order to solve the problems, the (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene is successfully synthesized by taking propargyl alcohol as an initial raw material and taking a Sharpless asymmetric dihydroxylation reaction as a key step without the step of the sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by trifluoromethanesulfonic anhydride in the preparation process. Therefore, the whole reaction is mild and controllable and few in side reactions, and enantioselectivity is high.
NUCLEOSIDE PRODRUGS AND USES RELATED THERETO
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Page/Page column 181; 182, (2021/02/26)
Disclosed are acyclic nucleoside prodrugs with improved metabolic stability and oral bioavailability. In general, the prodrugs are derivatives of acyclic nucleoside phosphonates containing a lipid-like moiety that can increase oral absorption and subsequent stability in the liver and plasma. Preferably, the lipid-like moiety can resist enzyme-mediated ω-oxidation, such as ω -oxidation catalyzed by cytochrome P450 enzymes. Also disclosed are pharmaceutical formulations of the acyclic nucleoside prodrugs. The acyclic nucleoside prodrugs and pharmaceutical formulations thereof can be used to treat viral infections, such as HIV infections, and/or viral-associated cancer, such as HPV-associated cancers.
ω-Functionalized Lipid Prodrugs of HIV NtRTI Tenofovir with Enhanced Pharmacokinetic Properties
Bartsch, Perry W.,Basson, Adriaan E.,Burton, Samantha L.,Bushnev, Anatoliy,D'Erasmo, Michael,Dasari, Madhuri,Derdeyn, Cynthia A.,Giesler, Kyle E.,Hwang, Soyon S.,Iskandar, Sabrina,Liotta, Dennis C.,Miller, Eric J.,Pribut, Nicole,Raghuram, Akshay,Sharma, Savita K.
supporting information, p. 12917 - 12937 (2021/09/13)
Tenofovir (TFV) is the cornerstone nucleotide reverse transcriptase inhibitor (NtRTI) in many combination antiretroviral therapies prescribed to patients living with HIV/AIDS. Due to poor cell permeability and oral bioavailability, TFV is administered as one of two FDA-approved prodrugs, both of which metabolize prematurely in the liver and/or plasma. This premature prodrug processing depletes significant fractions of each oral dose and causes toxicity in kidney, bone, and liver with chronic administration. Although TFV exalidex (TXL), a phospholipid-derived prodrug of TFV, was designed to address this issue, clinical pharmacokinetic studies indicated substantial hepatic extraction, redirecting clinical development of TXL toward HBV. To circumvent this metabolic liability, we synthesized and evaluated ω-functionalized TXL analogues with dramatically improved hepatic stability. This effort led to the identification of compounds 21 and 23, which exhibited substantially longer t1/2 values than TXL in human liver microsomes, potent anti-HIV activity in vitro, and enhanced pharmacokinetic properties in vivo.
Method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene
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Paragraph 0032-0034, (2021/06/23)
The invention belongs to the technical field of green pesticides, and discloses a novel method for synthesizing a main active component (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene of sex pheromone of fall webworms. The method comprises the steps: by taki
Membrane properties of amacrocyclic tetraether bisphosphatidylcholine lipid: Effect of a single membrane-spanning polymethylene cross-linkage between two head groups of ditetradecylphosphatidylcholine membrane
Tsuchida, Naoyuki,Takagi, Toshiyuki,Takahashi, Hiroshi,Yoshihara, Toshitada,Tobita, Seiji,Sonoyama, Masashi
, (2021/02/12)
The plasma membranes of archaea are abundant in macrocyclic tetraether lipids that contain a single or double long transmembrane hydrocarbon chains connecting the two glycerol backbones at both ends. In this study, a novel amacrocyclic bisphosphatidylcholine lipid bearing a single membrane-spanning octacosamethylene chain, 1,1’-O-octacosamethylene-2,2′-di-O-tetradecyl-bis-(sn-glycero)-3,3′-diphosphocholine (AC-(di-O-C14PC)2), was synthesized to elucidate effects of the interlayer cross-linkage on membrane properties based on comparison with its corresponding diether phosphatidylcholine, 1,2-di-O-tetradecyl-sn-glycero-3-phosphocholine (DTPC), that forms bilayer membrane. Several physicochemical techniques demonstrated that while AC-(di-O-C14PC)2 monolayer, which adopts a particularly high-ordered structure in the gel phase, shows remarkably high thermotropic transition temperature compared to DTPC bilayer, the fluidity of both phospholipids above the transition temperature is comparable. Nonetheless, the fluorescent dye leakage from inside the AC-(di-O-C14PC)2 vesicles in the fluid phase is highly suppressed. The origin of the membrane properties characteristic of AC-(di-O-C14PC)2 monolayer is discussed in terms of the single long transmembrane hydrophobic linkage and the diffusional motion of the lipid molecules.
Synthesis method of hyphantria cunea sex pheromone intermediate
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Paragraph 0043-0046, (2019/10/01)
The invention discloses a synthesis method of a hyphantria cunea sex pheromone intermediate. The method comprises the steps that 2-(2-propynyloxy)tetrahydropyran and a benzenesulfonate undecane compound (2) are taken as substrates, under the catalysis of a catalyst I, a reaction is carried out to obtain a compound (3), the compound (3) is hydrolyzed in an acidic environment to obtain a compound (4), the compound (4) is subjected to selective catalytic hydrogenation to obtain a cis-olefin compound (5), and finally, under the function of a catalyst II, a chiral reagent and an oxidant, (2S,3R)-2,3-epoxytetradecyl alcohol is obtained by Sharpless epoxidation. By means of the method, the hyphantria cunea sex pheromone intermediate can be efficiently and highly-selectively synthesized, and through simple crystallization treatment, the enantiomeric excess of the intermediate can reach the standard that the ee value is greater than 99%. The synthesis method has the advantages of short route and good corresponding selectivity.
Synthesis method of tetradec-2-yn-1-ol
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Paragraph 0030-0044, (2019/10/15)
The invention discloses a synthesis method of tetradec-2-yn-1-ol and belongs to the technical field of chemical industry production. According to the method, with acetylene as an initial raw material,the acetylene and alkali react in a solvent to generate acetylene salt; then, 1- bromoundecane is added for a reaction to obtain 1-tridecyne, the thirteen acetylene salt further reacts with paraformaldehyde or a formaldehyde aqueous solution or formaldehyde gas, and through a one-pot method, the tetradec-2-yn-1-ol is synthesized. The synthesis method is mild in reaction condition, easy and convenient to implement and low in production cost, has good economic benefits and can be applied and popularized, and the purity and yield of the product tetradec-2-yn-1-ol are high.
Activity-Based Probes for 15-Lipoxygenase-1
Eleftheriadis, Nikolaos,Thee, Stephanie A.,Zwinderman, Martijn R. H.,Leus, Niek G. J.,Dekker, Frank J.
supporting information, p. 12300 - 12305 (2016/10/13)
Human 15-lipoxygenase-1 (15-LOX-1) plays an important role in several inflammatory lung diseases, such as asthma, COPD, and chronic bronchitis, as well as various CNS diseases, such as Alzheimer's disease, Parkinson's disease, and stroke. Activity-based probes of 15-LOX-1 are required to explore the role of this enzyme further and to enable drug discovery. In this study, we developed a 15-LOX-1 activity-based probe for the efficient activity-based labeling of recombinant 15-LOX-1. 15-LOX-1-dependent labeling in cell lysates and tissue samples was also possible. To mimic the natural substrate of the enzyme, we designed activity-based probes that covalently bind to the active enzyme and include a terminal alkene as a chemical reporter for the bioorthogonal linkage of a detectable functionality through an oxidative Heck reaction. The activity-based labeling of 15-LOX-1 should enable the investigation and identification of this enzyme in complex biological samples, thus opening up completely new opportunities for drug discovery.
Tetris in monolayers: Patterned self-assembly using side chain shape
Xue, Yi,Zimmt, Matthew B.
supporting information; experimental part, p. 8832 - 8834 (2011/09/16)
The "kinked" shapes of conjugated alkadiynes constrain chain packing in monolayers on HOPG. Centrally located diyne units permit assembly of 1,5-bis(alkadiyne)anthracene monolayers. Off-center diynes inhibit self-assembly. Shape matched pairs of off-center diyne chains direct self-assembly of compositionally patterned, two component monolayers.
