Alok Singh, Hyun-Joon Ha, Jungchan Park, Jun Hee Kim, Won Koo Lee

 

 Heterocyclic analogs of ceramide as 3-alkanoyl or benzoyl-4-(1-hydroxy-2-enyl)-oxazolidin-2-ones were
designed by binding of primary alcohol and amide in sphinogosine backbone as a carbamate. They were
synthesized by addition of acyl halide to the common ring 4-(1-t-butyldimethylsilyloxyhexadec-2-enyl)-
oxazolidin-2-one which was elaborated from chiral aziridine-2-carboxylate including stereoselective
reduction and ring opening reactions as key steps. Other analogs with different carbon frame at C4
position which is corresponding to the sphingoid backbone were prepared from 3-cyclopentanecarbonyl-
4-(1-t-butyldimethylsilyloxybut-2-enyl)-oxazolidin-2-one and straight and cyclic alkenes by cross
metathesis. All compounds were tested as antileukemic drugs against human leukemia HL-60 cells. Many
of them including propionyl, cyclopentanoyl and p-nitrobenzoyl-4-(1-hydroxyhexadec-2-enyl)-oxazolidin-
2-ones showed better antileukemic activities than natural C2-ceramide with good correlation
between cell death and DNA fragmentation. There is a drastic change of the activities by the carbon chain
lengths at C4 position. Cytotoxicity was induced by caspase activation without significant accumulation
of endogenous ceramide concentration or any perturbation of ceramide metabolism.

 

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List of Articles
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88 88. Atom Economical Synthesis of Oxindoles by Metal-Catalyzed Intramolecular C-C Bond Formation under Solvent-Free and Aerobic Conditions, Green Chem., 2015, 17, 3306–3309 imagefile aziridine 2016-03-18 1520
87 87. N-Methylative aziridine ring opening: Asymmetric synthesis of hygroline, pseudohygroline, and hygrine, Tetrahedron Letters 56 (2015) 856–858 imagefile aziridine 2016-03-18 1448
86 86. One-pot Solvent-Free Reductive Amination with a Solid Ammonium Carbamate Salt from CO2 and Amine, RSC Adv., 2014, 4, 46203–46207 imagefile aziridine 2016-03-18 1389
85 85. Asymmetric Synthesis of Fluoroamines from Chiral Aziridines, Bull. Korean Chem. Soc. 2014, Vol. 35, No. 3 file aziridine 2016-03-18 2157
84 84. Synthesis and Biological Activities of Tyroscherin Analogs, Bull. Korean Chem. Soc. 2013, Vol. 34, No. 6 file aziridine 2016-03-18 1331
83 83. Highly Stereoselective Directed Reactions and an Efficient Synthesis of Azafuranoses from a Chiral Aziridine, Org Biomol Chem. 2013 Jun 14;11(22):3629-34 imagefile aziridine 2016-03-18 1118
82 82. CAL-B catalyzed desymmetrization of 3-alkylglutarate: "olefin effect" and asymmetric synthesis of pregabalin, Org. Biomol. Chem., 2013, 11, 3635 imagefile aziridine 2013-08-27 2399
81 81. Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine, Org. Biomol. Chem., 2013, 11, 3629 imagefile aziridine 2013-08-27 2439
80 80. Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine, Tetrahedron Lett., 2013, 54, 553 imagefile aziridine 2013-08-27 2182
79 79. Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine, Tetrahedron Lett., 2013, 54, 1384 imagefile aziridine 2013-08-27 2225
78 78. Chemoselective reduction of olefin by mixed "Pd" catalyst, Bulletin of the Korean Chemical Society (2012), 33(9), 2853-2854. imagefile aziridine 2013-05-30 2487
77 77. Highly improved copper-mediated Michael addition of ethyl bromodifluoroacetate in the presence of protic additive, Synthesis (2012), 44(20), 3165-3170. imagefile aziridine 2013-05-30 1827
76 76. The sphingosine-1-phosphate derivative NHOBTD inhibits angiogenesis both in vitro and in vivo, Biochemical and biophysical research communications (2011), 413(2), 189-93. file aziridine 2013-05-30 1796
75 75. Synthesis of 2,5-Disubstituted 6-Azaindoles from Substituted Aziridines via Intramolecular Cyclization, ORGANIC LETTERS, 2012, Vol. 14, No. 12, 3120–3122. imagefile aziridine 2012-06-11 2418
74 74. Alkylative Ring Opening of N-Methylaziridinium Ions and a Formal Synthesis of Tyroscherin, Org. Lett., 2012, Vol. 14, No. 2, 429–431 imagefile aziridine 2012-06-11 2438
73 73. Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines, Org. Biomol. Chem., 2011, 9, 1372 imagefile aziridine 2012-01-27 3054
72 72. Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles, Tetrahedron 68 (2012) 883-893 imagefile aziridine 2012-01-27 2835
» 71. 3,4-Disubstituted oxazolidin-2-ones as constrained ceramide analogs with anticancer activities. Bioorganic & Medicinal Chemistry 19 (2011) 6174–6181 imagefile aziridine 2012-01-27 3155
70 70. N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt. Tetrahedron Letters 52 (2011) 5918–5920 imagefile aziridine 2012-01-27 3087
69 69. Regiochemical Pathway in the Ring Opening of 2-Acylaziridines. Bull. Korean Chem. Soc. 2011, Vol. 32, No. 8 2879 imagefile aziridine 2012-01-27 3191
68 68. Synthesis of 1,2,5-and 1,2,3,5-substituted pyrroles from substituted aziridines via Ag(I)-catalyzed intramolecular cyclization , Tetrahedron 67 (2011) 3553-3556. imagefile aziridine 2011-05-06 3800
67 67. Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation-BMCL, 2008, 18, 5591-5593 imagefile aziridine 2010-09-27 4597
66 66. An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines - Tetrahedron, 2010, 66, 8108-8114 imagefile aziridine 2010-09-08 4517
65 65. A formal synthesis of (-)-swainsonine from a chiral aziridine - Tetrahedron Lett. 2010, 51, 3284 imagefile aziridine 2010-05-29 4853
64 64. Conjugate addition of amines to chiral 3-aziridin-2-yl-acrylates - Tetrahedron Lett. 2010, 2181 imagefile aziridine 2010-05-29 4925
63 63. Synthesis of substituted imidazolidin-2-ones as aminoacyl-tRNA synthase inhibitors - Bull.Kor.Chem.Soc. 2010, 611 imagefile aziridine 2010-05-29 4695
62 62. Molecular docking study of aminoacyl-tRNA synthetases with ligand molecules from four different scaffolds - Bull.Kor.Chem.Soc 2010, 606 imagefile aziridine 2010-05-29 4225
61 61. Molecular basis for the stereoselective ammoniolysis of N-alkyl aziridine-2-carboxylates catalyzed by Candida antarctica lipase B - ChemBioChem 2009, 10, 2213 imagefile aziridine 2010-05-29 4505
60 60. Synthesis of D-erythro-sphingosine from D-ribo-phytosphingoshine - Bull. Kor. Chem. Soc. 2009, 535 imagefile aziridine 2010-05-29 4290
59 59. [Synthetic ceramide analogs for anticancer agents] in Glycolipids New Research, Nova Science Pub. New York, 2008, 145- 156 imagefile aziridine 2010-05-29 4624


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