• 농약과학회지
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• 제5권2호
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• pp.33-36
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• 2001

2-Chloromethyl-1,3-dioxolane기가 치환된 새로운 thiophene sulfonylurea계 유도체들을 합성하였고, 신규 합성된 화합물을 발아전 토양처리와 발아후 경엽처리를 통하여 문제잡초 9종의 제초활성을 규명하였으며, 답작 조건의 이앙벼 및 주요 잡초에 대한 제초활성도 시험하였다. 이 화합물들의 제초활성은 헤테로고리의 치환기에 따라 매우 다르게 나타났는데, 4, 6 위치에 각각 dimethoxy, 혹은 methyl, methoxy가 치환된 pyrimidine, 혹은 triazine이 붙어있는 sulfonylurea들이 활성이 좋았다. 그러나 이들은 2-fluoromethyl-1,3-dioxolane기가 치환된 thiophene sulfonylurea계 유도체보다 일반적으로 제초활성이 약하게 나타났다.

• Bulletin of the Korean Chemical Society
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• 제25권2호
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• pp.260-262
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• 2004

In agreement with the results of previous MP2 calculations by Sauers, B3LYP, CASSCF, and CASPT2 calculations on the parent 2-carbena-1,3-dioxolane show that it fragments to ethylene plus $CO_2$ by a concerted pathway with only a small energy barrier. Not only is fragmentation via stepwise C-O bond cleavage computed to be a much higher energy pathway, but the singlet diradical that would be an intermediate along such a reaction path is not even computed to be a local minimum on the potential energy surface.

• 약학회지
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• 제38권6호
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• pp.775-781
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• 1994

$({\pm})-Dioxolane-T$ and$({\pm})-BCH-189$ are know to possess anti-HIV activities, and less to xicities compared to other dideoxynucleoside AIDS drugs. We have synthesized 34 different enantiomerically pure nucleosides by glycosylation of L-1,3-dioxolanyl acetate and L-1,3-oxathiolanyl acetate sugar moieties with uracil or 6-azauracil with alkyl chains$(C_1-C_3)$ on 5 or 6 position.

• Toxicological Research
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• 제8권2호
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• pp.205-216
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• 1992

cis-Malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]platinum(II)(SKI 2053R), an antitumor platinum complex, was selected for clinical evaluation on the basis of its experimental antitumor and toxicologic profiles in preclinical studies. These studies were performed to obtain information on its toxic signs, orgnas which are mainly affected, and to estimate its lethality in mice and rats given SKI 2053R through two routes of administration. In male and female rats given a single intragastrical dose of SKI 2053R, we estimated that $LD_{50}$ values were over 3.00g/kg, respectively. In male and female mice given a signle intragastrical dose of SKI 2053R, we estimated that $LD_{50}$ values were 2.44g/kg and 1.59g/kg, respectively, In a single intraperitoneal dose of SKI 2053R, we determined that $LD_{50}$ values of male and female rats were 227mg/kg and 182mg/kg, and those of male and female mice were 198mg/kg and 207mg/kg, respectively. In gross and histopathological examinations on dead animals, we found that kidney and liver were mainly affected.

• Natural Product Sciences
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• 제21권4호
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• pp.231-236
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• 2015

Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (3-6) by chemical investigation. Compounds 1 - 6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.

• 약학회지
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• 제40권1호
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• pp.46-51
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• 1996

Eight new D-1.3-dioxolanyl and L-1,3-oxathiolanyl nucleosides containing 5-phenyl- selenyl pyrimidine bases which are expected to have antiviral activity were synthesized. Condensation of D-1,3-dioxolane acetate and L-1,3-oxathiolane acetate with 5-phenylselenyl pyrimidines gave anomeric mixtures of their nucleosides which were separated by silicagel column chromatography.

• Bulletin of the Korean Chemical Society
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• 제16권8호
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• pp.769-773
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• 1995

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.73-73
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• 1993

As part of a research program to develope 3rd generation anti tumor platinum complexes, a series of platinum complexes which have 4, 5-bis-(aminomethyl)- 1, 3-dioxolane derivatives as bidenate amine ligands, represented by the general structual formula was prepared. The R$_1$ and/or R$_2$ substituents in this series of platinum complexes can be hydrogen. alkyl, of jointly formed cyclohexane. Two Xs can be a bidenate leaving ligand such as 1, 1-cyclobutanedicarboxylate, malonate, dimethylmalonate, ethylmalonate, glycolate, L-lactate, or N-methyliminodiacetate. From based on the pharmacological and toxicological studies, we have chosen SKI 2053R, cis-malonato[(4R, 5R)-4, 5-bis(aminomethyl)-2-isopropyl-1, 3-dioxolane] platinum(II) complex (NSC D644591) as a candidate for clinical evaluation. The antitumor activity of a new anti tumor platinum complex, cis-malonato [(4R, 5R)-4, 5-bis(aminomethyl)-2-isopropyl-1, 3-dioxolane] platinum(II) (SKI 2053R, NSC D644591), was compared with those of cisplatin and carboplatin using murine tumors. We evaluated three platinum complexes against L1210/CPR, a subline of L1210 leukemia resistant to cisplatin for their abilities to overcome tumor resistance to cisplatin. The in vitro cytotoxicity of SKI 2053R to L1210 cell line was 2.5-fold less potent thann that of cisplatin, and was 10-fold more cytotoxic than that of carboplatin. SKI 2053R retained similar cytotoxic effect and anti tumor activity to L1210/CPR cell line, like the cytotoxicity of SKI 2053R to L1210 cell line, while either cisplatin or carboplatin had not property to overcome the acquired cisplatin-resistance. SKI 2053R exhibited greater or comparable antitumor activity than cisplatin or carboplatin in murine tumor models.

• 약학회지
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• 제38권6호
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• pp.703-711
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• 1994

We synthesized D-1,3-dioxolanyl acetate from D-mannose using Frazer-Reide reaction and D-1,3-oxathiolanyl acetate from either D-mannose or D-galactose in good yields. These acetates were conjugated with various disilylated pyrimidine base using trimethylsilyl trifluoromethane sulfonate as a Lewis acid catalyst to obtain 32 different D-nucleosides.

• Toxicological Research
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• 제8권2호
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• pp.235-253
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• 1992

A subacute toxicity study of cis-Malonato[(4R,5R)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]platinum(II)(SKI 2053R) was carried out to obtain information on its toxicological profiles, and to determine the maximum tolerated dose in beagle dogs. Four groups of beagle dogs (2M and 2F per group, 0,0.5,1.0,2.0mg/kg/day)were given 15 i.v. injections of SKI 2053R. In order to compare the toxic effects of SKI 2053R with those of cisplatin, one group was treated with cisplatin(0.7mg/kg/day)according to the same treatment schedule. The dosing schedule was divided into 3 courses of 5 consecutive days with 23-day dose-free intervals between each course. After completion of the treatments, remaining dogs were necropsied under established guidelines. Three of four dogs in the high dose group and one of four dogs in the middle dose group treated with SKI 2053R died of hypovolemic shock secondary to hemorrhagic and ulcerative enterocolitis. No toxicity-related mortality occurred in the low dose group of SKI 2053R. No survivor was observed in the group of cisplatin. Clinical signs including vomiting, diarrhea, anorexia and loss body weight were apparent in dogs given either cisplatin or high and middle doses of SKI 2053R. Severe thrombocytopenia and leukocytopenia were observed in the high dose group of SKI 2053R and cisplatin-treatment group, while toxicities as bone marrow suppression were reversible. The significant elevation of serum ALP values in group of SKI 2053R(2.0 mg/kg/day and 1.0mg/kg/day) and cisplatin(0.7mg/kg/day)was observed. Slight proteinuria waa observed in high and middle dose level groups of SKI 2053R. In histopathological examinations, pathological alterations of liver, kidney and spleen were noted dose-dependantly in dogs treated with SKI 2053R, and there was no overt sign of toxicity in low dose group of SKI 2053R. Compared to SKI 2053R, more severe durg-related toxicities occurred in dogs treated with cisplatin. It waw estimated that maximum tolerated dose of SKI 2053R in this treatment schedule was 0.5~0.7mg/kg/day. In conclusion, overall toxic potential of SKI 2053R was approximately 3 times lower than that of cisplatin with respect of lethality.