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 2016-03-18 904
87 87. N-Methylative aziridine ring opening: Asymmetric synthesis of hygroline, pseudohygroline, and hygrine, Tetrahedron Letters 56 (2015) 856–858 imagefile aziridine 2016-03-18 891
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 2016-03-18 837
85 85. Asymmetric Synthesis of Fluoroamines from Chiral Aziridines, Bull. Korean Chem. Soc. 2014, Vol. 35, No. 3 file aziridine 2016-03-18 853
84 84. Synthesis and Biological Activities of Tyroscherin Analogs, Bull. Korean Chem. Soc. 2013, Vol. 34, No. 6 file aziridine 2016-03-18 795
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 2016-03-18 739
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 1895
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 1912
80 80. Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine, Tetrahedron Lett., 2013, 54, 553 imagefile aziridine 2013-08-27 1811
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 1815
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 1843
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 1477
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 1431
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 1990
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 1963
73 73. Asymmetric synthesis of 1-deoxyazasugars from chiral aziridines, Org. Biomol. Chem., 2011, 9, 1372 imagefile aziridine 2012-01-27 2708
72 72. Chiral aziridine-2-carboxylates: versatile precursors for functionalized tetrahydroisoquinoline (THIQ) containing heterocycles, Tetrahedron 68 (2012) 883-893 imagefile aziridine 2012-01-27 2487
» 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 2667
70 70. N-Methylative aziridine ring opening and asymmetric synthesis of MeBmt. Tetrahedron Letters 52 (2011) 5918–5920 imagefile aziridine 2012-01-27 2672
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 2772
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 3370
67 67. Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation-BMCL, 2008, 18, 5591-5593 imagefile aziridine 2010-09-27 4179
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 4170
65 65. A formal synthesis of (-)-swainsonine from a chiral aziridine - Tetrahedron Lett. 2010, 51, 3284 imagefile aziridine 2010-05-29 4453
64 64. Conjugate addition of amines to chiral 3-aziridin-2-yl-acrylates - Tetrahedron Lett. 2010, 2181 imagefile aziridine 2010-05-29 4510
63 63. Synthesis of substituted imidazolidin-2-ones as aminoacyl-tRNA synthase inhibitors - Bull.Kor.Chem.Soc. 2010, 611 imagefile aziridine 2010-05-29 4271
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 3840
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 4104
60 60. Synthesis of D-erythro-sphingosine from D-ribo-phytosphingoshine - Bull. Kor. Chem. Soc. 2009, 535 imagefile aziridine 2010-05-29 3893
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 4200


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