- Convenient synthesis of 3-(S)-amino-γ-butyrolactone
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An efficient two step conversion of N-t-Boc-L-aspartic acid β-benzyl ester to enantiopure 3-(S)-amino-γ-butyrolactone is described. In this route, chemoselective reduction of the α-carboxylic group in the starting material via a mixed anhydride with NaBH4 afforded the corresponding alcohol in 95% yield without any loss of the optical purity. Subsequent acidic hydrolysis of the N-protected β-amino alcohol not only deprotected the amino group, but also produced the desired γ-lactone in 98% yield with complete retention of the optical activity.
- Sibrian-Vazquez, Martha,Spivak, David A.
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- Rational design, synthesis and in vitro evaluation of novel exo-methylene butyrolactone salicyloylamide as NF-κB inhibitor
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(?)-Dehydroxymethylepoxyquinomicin ((?)-DHMEQ, 1) is a specific inhibitor of NF-κB. It binds to SH group in the specific cysteine residue of NF-κB components with its epoxide moiety to inhibit DNA binding. In the present research, we have designed and synthesized an epoxide-free analog called (S)-β-salicyloylamino-α-exo-methylene-?-butyrolactone (SEMBL, 3). SEMBL inhibited DNA binding of NF-κB component p65 in vitro. It inhibited LPS-induced NF-κB activation, iNOS expression, and inflammatory cytokine secretions. It also inhibited NF-κB and cellular invasion in ovarian carcinoma ES-2 cells. Moreover, its stability in aqueous solution was greatly enhanced compared with (?)-DHMEQ. Thus, SEMBL has a potential to be a candidate for a new anti-inflammatory and anticancer agent.
- Sidthipong, Kulrawee,Ma, Jun,Yu, Wei Lin,Wang, Yan Feng,Kobayashi, Susumu,Kishino, Satoshi,Koide, Naoki,Yokochi, Takashi,Kato, Kuniki,Okada, Shoshiro,Umezawa, Kazuo
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p. 562 - 566
(2017/01/17)
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- CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF
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The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.
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Page/Page column 19; 20
(2015/05/19)
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- Fibrinogen receptor antagonists
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Fibrinogen receptor antagonists having the structure, for example, of STR1 for example STR2
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- Synthesis of enantiomerically pure β-amino-α-methylene-γ-butyrolactones by way of ozonolysis of aromatic α-amino acids
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The (R) and (S) isomers of β-amino-α-methylene-γ-butyrolactone hydrochloride (4-amino-dihydro-3-methylene-2(3H)-furanone hydrochloride) have been synthesized from (R)- and (S)-tryptophan, respectively.A key step is the ozonolysis of N,O-diacetyl-2-amino-3-(3'-indolyl)-1-propanol. (S)-β-Amino-α-methylene-γ-butyrolactone hydrochloride has been synthesized also by an analogous route starting with (S)-phenylalanine.
- Hvidt, Torsten,Szarek, Walter A.,Maclean, David B.
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p. 779 - 782
(2007/10/02)
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