112-90-3Relevant articles and documents
Rapid phosphine-free synthesis of CdSe quantum dots: Promoting the generation of Se precursors using a radical initiator
Hou, Bo,Benito-Alifonso, David,Webster, Richard,Cherns, David,Galan, M. Carmen,Fermin, David J.
, p. 6879 - 6886 (2014)
The replacement of phosphine containing compounds in the synthesis of II-VI quantum dots (QDs) via the 'hot-injection' method has received considerable attention in recent years, in particular toward scaling-up production. A key bottleneck in current appr
Photoinduced remote regioselective radical alkynylation of unactivated C-H bonds
Hu, Qu-Ping,Liu, Yong-Ze,Liu, Yu-Tao,Pan, Fei
, p. 2295 - 2298 (2022/02/25)
A method for the remote regioselective alkynylation of unactivated C(sp3)-H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.
Direct Enzymatic Synthesis of Fatty Amines from Renewable Triglycerides and Oils
Bevinakatti, Han,Citoler, Joan,Finnigan, William,Turner, Nicholas J.
, (2021/11/30)
Fatty amines represent an important class of commodity chemicals which have broad applicability in different industries. The synthesis of fatty amines starts from renewable sources such as vegetable oils or animal fats, but the process has multiple drawbacks that compromise the overall effectiveness and efficiency of the synthesis. Herein, we report a proof-of-concept biocatalytic alternative towards the synthesis of primary fatty amines from renewable triglycerides and oils. By coupling a lipase with a carboxylic acid reductase (CAR) and a transaminase (TA), we have accomplished the direct synthesis of multiple medium and long chain primary fatty amines in one pot with analytical yields as high as 97 %. We have also performed a 75 mL preparative scale reaction for the synthesis of laurylamine from trilaurin, obtaining 73 % isolated yield.
CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
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Paragraph 0248, (2020/11/27)
Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).
Simplifying the Chemical Structure of Cationic Lipids for siRNA-Lipid Nanoparticles
Kuboyama, Takeshi,Yagi, Kaori,Naoi, Tomoyuki,Era, Tomohiro,Yagi, Nobuhiro,Nakasato, Yoshisuke,Yabuuchi, Hayato,Takahashi, Saori,Shinohara, Fumikazu,Iwai, Hiroto,Koubara-Yamada, Ayumi,Hasegawa, Kazumasa,Miwa, Atsushi
supporting information, p. 749 - 753 (2019/05/06)
We report a potent cationic lipid, SST-02 ((3-hydroxylpropyl)dilinoleylamine), which possesses a simple chemical structure and is synthesized just in one step. Cationic lipids are key components of siRNA-lipid nanoparticles (LNP), which may serve as potential therapeutic agents for various diseases. For a decade, chemists have given enhanced potency and new functions to cationic lipids along with structural complexity. In this study, we conducted a medicinal chemistry campaign pursuing chemical simplicity and found that even dilinoleylmethylamine (SST-01) and methylpalmitoleylamine could be used for the in vitro and in vivo siRNA delivery. Further optimization revealed that a hydroxyl group boosted potency, and SST-02 showed an ID50 of 0.02 mg/kg in the factor VII (FVII) model. Rats administered with 3 mg/kg of SST-02 LNP did not show changes in body weight, blood chemistry, or hematological parameters, while the AST level decreased at a dose of 5 mg/kg. The use of SST-02 avoids a lengthy synthetic route and may thus decrease the future cost of nucleic acid therapeutics.
A biocatalytic cascade for the conversion of fatty acids to fatty amines
Citoler, Joan,Derrington, Sasha R.,Galman, James L.,Bevinakatti, Han,Turner, Nicholas J.
supporting information, p. 4932 - 4935 (2019/09/30)
Fatty amine synthesis from renewable sources is an energetically-demanding process involving toxic metal catalysts and harsh reaction conditions as well as selectivity problems. Herein we present a mild, biocatalytic alternative to the conventional amination of fatty acids through a one-pot tandem cascade performed by a carboxylic acid reductase (CAR) and a transaminase (ω-TA). Saturated and unsaturated fatty acids, with carbon chain lengths ranging from C6 to C18, were successfully aminated obtaining conversions of up to 96%.
Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
, p. 3224 - 3230 (2018/04/23)
N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
LIPID NANO PARTICLES COMPRISING COMBINATION OF CATIONIC LIPID
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Paragraph 0254; 0261; 0263, (2014/03/21)
The present invention provides a lipid nano-particles, which allow nucleic acids to be easily introduced into cells, comprising a cationic lipid represented by formula (I) (wherein: R1 and R2 are, the same or different, alkenyl, etc, and X3 is absent or is alkyl, etc, X1 and X2 are hydrogen atoms, or are combined together to form a single bond or alkylene, and Y1 is absent or anion, L1 is a single bond, etc, R3 is alkyl, etc), and a cationic lipid represented by formula (II) (wherein: R4 and R5 are, the same or different, alkenyl, etc, and X4 and X5 are hydrogen atoms, or are combined together to form a single bond or alkylene, and X6 is absent or is alkyl, etc, Y2 is absent or anion, a and b are, the same or different, 0 to 3, and L4 is a single bond, etc, R6 is alkyl, etc, L2 and L3 are —O—, —CO—O— or —O—CO—), and the like.
RNAi PHARMACEUTICAL COMPOSITION FOR SUPPRESSING EXPRESSION OF KRAS GENE
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Paragraph 0180; 0187; 0189, (2014/03/21)
The present invention provides a composition for suppressing the expression of a KRAS gene, comprising a lipid particle containing, as a drug, a double-stranded nucleic acid having an antisense strand having a sequence of bases complementary to the sequence of at least 19 continuous bases of any one KRAS gene's mRNA of sequence Nos. 1 to 3; and a cationic lipid represented by the following formula (I): wherein R1 and R2, which are the same or different, are each linear or branched alkyl, alkenyl or alkynyl having a carbon number of from 12 to 24; L1 and L2, which are the same or different, are each —CO—O— or —O—CO—; a and b, which are the same or different, are each 1 to 3; and R3 is a hydrogen atom, alkyl having a carbon number of from 1 to 6, or alkenyl having a carbon number of from 3 to 6, and the like.
Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
, p. 5188 - 5197 (2013/09/02)
Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
