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Synthesis and Biological Evaluation of Novel Thioapio Dideoxynucleosides
Moon, Hyung Ryong,Kim, Hea Ok,Lee, Sang Kook,Choi, Won Jun,Chun, Moon Woo,Jeong, Lak Shin 梨花女子大學校 藥學硏究所 2002 藥學硏究論文集 Vol.- No.11
On the basis of the bioisosteric rationale to apio dideoxynucleosides. novel thioapio dideoxynucleosides have been syn-thesized, starting from 1,3-dihydroxyacetone via thioapio sugar acetate 6 as a key intermediate. The intermediate 6 was condensedwith silylated pyrimidine bases such as N^4-benzoylcytosine, uracil or thymine inl the presence of TMSOTf to give the β-anomers (8a,1la, and 12a) and α-anomers (8b, llb, and 12b), respectively. The intermediate 6 was also condensed with silyiated 6-chloropurineto give the 6-chloropurine derlvatives 14a and 14b which were converted to adenine derivatives 15a and 15b, N^6-methyladeninederivatives 16a and 16b, and hypoxanthine derivatives 17a and 17b. respectively. The guanine analogues 20a and 20b were alsosynthesiaed from the condensation of sugar acetate 6 with 2-acetamido-6-chlororurine . All synthesized fina1 compound swere testedaSainst HIV-1. Most of the synthesized compounds exhibited toxiclty-dependent anti-HIV-1 activity, among which 6-chloropurinederivative 14b was found to be the most cytotoxic and showed good cytotoxicity against colon cancer ceil lines. Although we couldnot find good anti-HIV agents in this study, findings of some anticancer activity in this series will allow this class of nucleosides tobe the new template for the development of new anticancer agents (Fig. 1).
Moon, Hyung Ryong,Park, Ah-Young,Kim, Kyung Ran,Chun, Moon Woo,Jeong, Lak Shin MARCEL DEKKER INC 2007 NUCLEOSIDES NUCLEOTIDES AND NUCLEIC ACIDS Vol.26 No.8-9
<P> Pseudo-l-vinylcyclopropyl adenine and guanine nucleosides 11 and 12 were designed and enantiopurely synthesized starting from (S)-epichlorohydrin using tandem alkylation, regioselective oxirane-ring opening, and chemoselective reduction as key steps.</P>
Moon, Hyung Ryong,Kim, Hea Ok,Lee, Kang Man,Chun, Moon Woo,Kim, Joong Hyup,Jeong, Lak Shin 梨花女子大學校 藥學硏究所 2002 藥學硏究論文集 Vol.- No.11
A total synthesis of apio-neplanocin A, which combines properties of apio nucleoside and neplanocin A and is a potential Inhibitor of S-adenisylhomocysteine hydrolase, was accomplished starting from D-ribose via stereoselective hydroxymethylation and RCM reaction.
Synthesis of 2',3'-didehydro-2',3'-dideoxy-2'-fluoro apionucleosides as potential antiviral agents
Moon, Hyung Ryong,Kim, Hea Ok,Jeong, Lak Shin 梨花女子大學校 藥學硏究所 2002 藥學硏究論文集 Vol.- No.11
Synthesis of novel 2', 3'-sisehydro-2',3'-dideoxy-2'-fluoro apionucleosides which combine the properties of 2', 3'-didehydro-2', 3'-dideoxy nucleosides and apionucleosides on the basis of a bioisosteric rationale is described.
Design, Synthesis, and In Vitro Evaluation of APIO Analogue of Neplanocin A
Moon, Hyung Ryong,Kwon, Sung Hee,Lee, Jeong Ah,Yoo, Byul Nae,Kim, Hea Ok,Chun, Moon Woo,Kim, Hee-Doo,Kim, Joong Hyup,Jeong, Lak Shin 梨花女子大學校 藥學硏究所 2003 藥學硏究論文集 Vol.- No.12
A novel apio analogue of neplanocin A was efficiently synthesized from D-ribose via stereoselective aldol-retroaldol reaction for introducing hydroxymethyl group and RCM reaction for synthesizing carbocycle, and its inhibitory activity against SAH hydrolase was assayed.
Synthesis of 5'-substituted fluoro-neplanocin A analogues
Moon, Hyung-Ryong,Lee, Hyun-Joo,Kim, Kyung-Ran,Lee, Kang-Man,Lee, Sang-Kook,Kim, Hea-Ok,Chun, Moon-Woo,Jeong, Lak-Shin 이화여자대학교 약학연구소 2004 藥學硏究論文集 Vol.- No.14
Four 5'-substituted fluoro-neplanocin A analogues la-d were designed and synthesized, using cyclopentenone derivative 2 as a key intermediate. The inhibitory activity against SAH was in the following order: NH₂>SH>F, N₃, indicating a hydrogen bonding donor such as OH or NH₂was essential for inhibitory activity. All the final compounds showed much less decreased cytotoxicity in two cancer cell lines(Col2 and A549), implying that phosphorylation of the 5'-hydroxyl group of fluoro-neplanocin A is closely related to its high cytotoxicity.
Asymmetric Synthesis and Biological Activity of l-Bicyclocarba-d4T
Moon, Hyung Ryong,Park, Ah-Young,Kim, Kyung Ran,Chun, Moon Woo,Jeong, Lak Shin Taylor Francis 2007 Nucleosides, nucleotides & nucleic acids Vol.26 No.10
<P> Novel l-bicyclocarba-d4T (1), an enantiomer of d-N-MCd4T has been enantiopurely synthesized as a potent anti-HIV agent starting from (R)-epichlorohydrin using tandem alkylation, chemoselective reduction of ester in the presence of lactone functional group, Grignard reaction, RCM reaction, and Mitsunobu reaction as key steps. l-N-MCd4T (1) was found to be very potent anti-HIV-1 (EC50 = 6.76 μg/mL) agent with no cytotoxicity.</P>
Acyclonucleoside 류의 합성(3) -Ribavirin 유도체의 합성-
문형룡(Hyung Ryong Moon),양재욱(Jae Wook Yang),김문환(Moon Hwan Kim),천문우(Moon Woo Chun),정원근(Won Keun Chung) 대한약학회 1989 약학회지 Vol.33 No.6
The Synthesis of acyclic derivatives of ribavirin (2''-azido and halo seco derivatives) for the development of new antiviral agents is described. These acyclic nucleosides are synthesized from ribavirin by the method of ring opening reaction of sugar moietry.