• Archives of Pharmacal Research
• /
• 제27권7호
• /
• pp.713-719
• /
• 2004

Several analogues of the general formulae 2-methoxy-9-substituted acridine and 6-chloro-2-methoxy-9-substituted acridine were synthesized and evaluated in vitro at 6.25 $\mu\textrm{g}$/mL against M. tuberculosis $H_{37}Rv$. Compounds 15 and 17 showed potential antitubercular activity with 100％ inhibition to the virulent mycobacterium.

• Archives of Pharmacal Research
• /
• 제26권9호
• /
• pp.667-678
• /
• 2003

We examined the effect of p-substituents in p-substituted cinnamyl methyl ethers and 1-(p-substituted phenyl)allyl methyl ethers with CSI, and confirmed that the CSI reaction of allyl ethers (p-substituted ethers) is a competitive reaction of $S_Ni{\;}and{\;}S_N1$ mechanism according to the stability of the carbocation. And, the only terminal allylic amine was obtained through the migration reaction in thermodynamic reaction condition.

• Archives of Pharmacal Research
• /
• 제21권6호
• /
• pp.753-758
• /
• 1998

Sixteen novel 2-substituted acetyl amino-5-alkyl-1,3,4-thiadiazol were synthesized and screened for their pharmacological activities. A few of the compounds namely 11, 12 and 16 showed anti-inflammatory activities comparable to phenylbutazone. Compound 12 also showed significan non-specific spasmolytic activity. Diuretic activity of compound 15 at a dose level of 90mg/kg p.o. was two fold higher compared to 50mg/kg p.o. of furosemide. Comparable diuresis was aso produced by compounds 9, 10, and 16.

• Parasites, Hosts and Diseases
• /
• 제55권6호
• /
• pp.661-665
• /
• 2017

We synthesized C-10 substituted triazolyl artemisinins by the Huisgen cycloaddition reaction between dihydroartemisinins (2) and variously substituted 1, 2, 3-triazoles (8a-8h). The antimalarial activities of 32 novel artemisinin derivatives were screened against a chloroquine-resistant parasite. Among them, triazolyl artemisinins with electron-withdrawing groups showed stronger antimalarial activities than those shown by the derivatives having electron-donating groups. In particularly, m-chlorotriazolyl artemisinin (9d-12d) showed antimalarial activity equivalent to that of artemisinin and could be a strong drug candidate.

• 약학회지
• /
• 제31권2호
• /
• pp.92-97
• /
• 1987

The N-[1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxy] succinimide was reacted with amoxicillin, ampicillin and 6-APA to give 6-[D-(-)-$\alpha$-{1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroguinoline-3-carboxamido} p-hydroxyphanyl acetamido] penicillanic acid [1], 6-[D-(-)-$\alpha$-{1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxamido} phenylacetamido] penicillanic acid [10] and 6-[1H-6-fluoro-1,4-dihydro-4-oxo-7-chloroquinoline-3-carboxamido] penicillanic acid [19]. The 1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxylic acids were reacted with ethyl chloroformate for making mixed anhydride; these mixed anhydrides were reacted with amoxicillin, ampilcillin and 6-APA to give 6-[D-(-)-$\alpha$-{1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido} p-hydroxyphenylacetamido] penicillanic acid [2-9], 6-[D-(1)-$\alpha$-{1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido} phenylacetamidod penicillanic acid [11-18] and 6-[1-alkyl-6-fluoro-1,4-dihydro-4-oxo-7-substituted quinoline-3-carboxamido] penicillanic acid [20-27].

• 한국응용약물학회:학술대회논문집
• /
• 한국응용약물학회 1997년도 춘계학술대회
• /
• pp.70-70
• /
• 1997

$\beta$-Lactamase 억제제로 6-Substituted exomethylene기를 갖는 penam계 화합물이 강력한 활성을 보여주고 있어서, $\beta$-lactamase억제제의 중간체 합성으로 6-exomethylene기에 도입 할 1-substituted thioalkyl-1,2,3-triazole-4-carboxaldehyde를 합성하였다. 2-Bromoethanol에 NaN$_3$를 반응시켜서 2-Azidoethanol을 합성하였고, 이것을 propargyl aldehyde와 반응시켜서 1-(2-hydroxyethyl)-1,2,3-triazole-4-carboxaldehyde를 합성하였다. 이것을 trifluoromethanesulfonic anhydride와 triethylamine존재 하에 heterocyclic mercapto화합물과 반응시켜서 hetorocyclic ring을 함유한 1-substituted thioalkyl-1,2,3-triazole-4-carboxaldehyde를 합성하였다.

• Bulletin of the Korean Chemical Society
• /
• 제23권2호
• /
• pp.262-266
• /
• 2002

Computations are presented for the ortho- and para-substituted benzyl alcohol-$H_2O$ clusters. A variety of conformers are predicted, and their relative energies are compared. Binding energies of the clusters are computed, and detailed analysis is presented on the effects of substitution on the strength of the hydrogen bond in the clusters. F- and $NH_2-$ substituted clusters are studied to analyze the effects of electron-withdrawing and electron-pushing groups. In para-substituted clusters, the inductive effects are dominant, affecting the binding energies in opposite way depending on whether the hydroxyl group is proton-donating or -accepting. For ortho-substituted clusters, more direct involvement of the substituting group and the resulting geometry change of the hydrogen bond should be invoked to elucidate complicated pattern of the binding energy of the clusters.

• 대한화학회지
• /
• 제58권6호
• /
• pp.569-574
• /
• 2014

The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-${\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

• Archives of Pharmacal Research
• /
• 제21권2호
• /
• pp.193-197
• /
• 1998

A number of substituted isoquinolin-1-ones, possible bioisosteres of the 5-aryl substituted 2,3-dihydroimidazo[2,$1-a$]isoquinolines, were synthesized and tested for their antitumor activity against five different human tumor cell lines. O-(3-hydroxyporpyl) substituted compound (15) exhibited the best antitumor activity which is 3-5 times better than 5-[$4^1$-(piperidinomethyl)phenyl]-2,3-dihydroimidazo[2,$1-a$]isoquinoline (1).

• 대한화학회지
• /
• 제8권4호
• /
• pp.153-157
• /
• 1964

Chloromethylation, malonic ester 합성법 및 decarboxylation에 의한 중간체들을 거친 tert.-butyl ${\beta}$-(o-tolyl)-perpropionate 치환체들의 합성을 기술하였다. 심하지 않은 치환기효과를 나타내는 bromo-, chloro- 및 methyl- 기를 가진 중간체들은 좋은 수율로 얻어져서 목적한 바 과산화 ester들을 얻었으나 nitro기를 가진 중간체는 극히 적은 수율로 얻어졌고 한편 센 electron donating effect를 나타내는 group로 치환된 toluene들의 chloromethylation은 polymerize하는 결과를 가져왔다.