• 제목/요약/키워드: carboxylic acid

검색결과 705건 처리시간 0.042초

A Series of Quinoline-2-carboxylic Acid Derivatives: New Potent Glycine Site NMDA Receptor Antagonists

  • 김란희;최진일;최승원;이광숙;정영식;박우규;성철민;박노상
    • Bulletin of the Korean Chemical Society
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    • 제18권9호
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    • pp.939-945
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    • 1997
  • Several types of 4-substituted-quinoline-2-carboxylic acid derivatives possessing different substituents at C4-position such as sulfonyl, phosphonyl, carbonyl groups, or a flexible alkyl chain have been synthesized and evaluated for their in vitro antagonistic activity at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Of them, 5,7-dichloro-4-(tolylsulfonylamino)-quinoline-2-carboxylic acid 9 was found to have the best in vitro binding affinity with IC50 of 0.57 μM. On the other hand, in compounds 21 and 22 the introduction of flexible alkyl chains on C4 of the quinoline mother nuclei caused a significant decrease of the in vitro binding affinity. In addition, replacement of polar carboxylic acid group on C2 by neutral bioisosteres in compounds 23a-d also seems to be disadvantageous to in vitro activity. In the structure-activity relationship (SAR) study of the 4-substituted quinoline-2-carboxylic acid acid derivatives, it was realized that the substitution pattern on C4 significantly influences on the binding affinity for the glycine site of NMDA receptor and the binding affinity might be increased by the introduction of a suitable electron rich substituent at C4 which has the ability of H-bonding donor.

1,4-Dihydropyridine-5-Formyl 유도체의 합성 (Synthesis of 1,4-Dihydropyridine-5-Formyl Derivatives)

  • 홍유화;서정진
    • 약학회지
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    • 제33권5호
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    • pp.290-295
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    • 1989
  • 2,6-Dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (1) was formylated to 2,6-dimethy-4-(3'-nitrophenyl)-5-formyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (2) in 76% yield. At the elevated temperature, 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-monomethyl ester (3) was also converted into compound 2 in 46% yield. The compound 2 was reduced to 2,6-dimethyl-4-(3'-nitrophenyl)-5-hydroxymethyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (4) in 91% yield. Compound 2 was reacted with triethyl phosphonoacetate to give 2,6-dimethyl-4-(3'-nitrophenyl)-5-(2-ethoxycarbonyl ethenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester (5) in 50% yield. Reaction between compound 2 and amines (methyl amine, ethylamine, methoxylamine, hydroxyl amine, phenyl hydrazine and 1-amino-4-methyl piperazine) gave six schiff bases 7a, 7b, 7c, 7e, 7f in 81%, 91%, 82%, 81%, 50% and 84% yield, respectively.

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6,6-Dichlorobicyclo[3, 1, 0]hexane-3-carboxylic acid의 합성과 분석 (Synthesis and Analysis of 6,6-dichlorobicyclo[3, 1, 0]hexane-3-carboxylic acid)

  • 이광수;양재건
    • 분석과학
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    • 제14권1호
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    • pp.1-7
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    • 2001
  • 6,6-Dichlorobicyclo[3, 1, 0]hexane-3carboxylic acid를 phase transfer catalyst(PTC)로 benzyl triethylamine chloride(BTEA.Cl)를 사용하여 3-cyclopentenecarboxylic acid로부터 합성하였다. $^1H$ NMR과 $^{13}C$ NMR 분석을 통하여 이 화합물은 boat-like conformation을 갖는 것으로 나타났고 carboxyl group은 trans로 존재하는 것으로 나타났다.

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Synthesis of 7-Hydroxy-4-Oxo-4H-Chromene- and 7-Hydroxychroman-2-Carboxylic Acid N-Alkyl Amides and Their Antioxidant Activities

  • Kwak, Jae-Hwan;Kang, Hae-Eun;Jung, Jae-Kyung;Kim, Hwa-Jung;Cho, Jung-Sook;Lee, Hee-Soon
    • Archives of Pharmacal Research
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    • 제29권9호
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    • pp.728-734
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    • 2006
  • A series of 7-hydroxy-4-oxo-4H-chromene- (3a - h) and 7-hydroxychroman-2-carboxylic acid N-alkyl amides (4a - g) were synthesized and their antioxidant activities were evaluated. While compounds 3a - h were less active, compounds 4a - g exhibited more potent inhibition of lipid peroxidation initiated by $Fe^{2+}$ and ascorbic acid in rat brain homogenates. Among them, 7-hydroxychroman-2-carboxylic acid N-alkylamides (4e - g) bearing nonyl, decyl, and undecyl side chain exhibited 3 times more potent inhibition than trolox (1).

Synthesis and Screening of Some Novel 2-[5-(Substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles as Potential Antimicrobial Agents

  • Gadegoni, Hemalatha;Manda, Sarangapani;Rangu, Shivaprasad
    • 대한화학회지
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    • 제57권2호
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    • pp.221-226
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    • 2013
  • A series of some novel 2-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-yl]-benzoxazoles were synthesized by using benzoxazole-2-carboxylic acid on reaction with thionyl chloride in presence of ethanol solvent at room temperature gave benzoxazole-2-carbonyl chloride, which is turned into benzoxazole-2-carboxylic acid hydrazide on reaction with hydrazine hydrate in ethanol solvent under reflux. The subsequent treatment of benzoxazole-2-carboxylic acid hydrazide with an appropriate aromatic carboxylic acid in presence of polyphosparic acid under reflux afforded the title compounds. The chemical structures of the newly synthesized compounds were elucidated by their IR, $^1H$ NMR and Mass spectral data analysis. Further the compounds are used to find out their ability towards anti microbial and nematicidal activity.

헤테로형 불소계 소화약제의 물리적 특성에 관한 연구 (Synthesis and Surface Activities of Perfluoro Hetero Type compounds)

  • 이승열;박노춘
    • 한국안전학회지
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    • 제13권1호
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    • pp.64-69
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    • 1998
  • Three kinds of N-fluoroacyl carboxy pyridinium chlorides were synthesized by the reaction of pyridine-carboxylic acid such as pyridine-2-carboxylic, pyridine-3-carboxylic and pyridine-4-carboxylic acid with long chain perfluoroacyl chloride. The surface chemical properties including surface tension, foaming power, foam stability, effectiveness of wettability and solubilizing effect were measured. These compounds showed good surface activities as emulsifying agent, solubilizing agent and fire-fighting agent.

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Morphology of Metal Salt of Carboxylic Acid: Metal and Acid Dependency on Branched Round Cluster Images

  • Min Su Kang;Kwang-Jin Hwang
    • 대한화학회지
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    • 제67권4호
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    • pp.222-225
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    • 2023
  • Metallic salts of C10-18 aliphatic carboxylic acids were prepared and their scanning electron microscopic images were analyzed for the morphology dependency with the metal and the carboxylic acid. Regardless of metal ion, metal salts of dicarboxylic acids showed a high crystallinity with a fiber image (SuA-Na). The aromatic dicarboxylates also represented a morphology of a rectangular-rod or board shapes (IA-Li, IA-Ba). With Na ion, most aliphatic carboxylate (MA, PA, SA) showed a fiber-like crystallinity. However, other monovalent Li, K and multivalent Mg, especially Al ion resulted a glassy-amorphous in the metallic salts of acids (MA, PA, SA). With divalent Ba and Ca ions, the metal salt of aliphatic acids expressed a branched round cluster shape as in SA-Ca, SA-Ba. Both Li and Mg ions with a similar size showed a strong morphological similarity in the metallic salts of aliphatic acids MA, PA, SA. In the case of Na and Ca ions with a similar size (98, 106 pm), both ionic salts of stearic acid gave a branching effect for a fiber or round granular image. In the case of hydroxyl-aliphatic acids (HLA, HPA, HSA), the fiber images in HLA-Na and HSA-Na was appeared about 100 nm thicker than those of nonhydroxycarboxylates (LA-Na, SA-Na). The metallic salts of unsaturated C-18 carboxylic acids (OlA, LeA and LnA) showed an amorphous glassy image due to a kinked carbon chain.

Some Recommended Procedures for Conversion of Carboxylic Acid and Its Derivatives to Aldehydes by Metal Hydride Reductions

  • Cha, Jin Soon
    • 통합자연과학논문집
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    • 제5권2호
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    • pp.84-90
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    • 2012
  • Some recommended procedures for obtaining aldehydes from carboxylic acid itself and its derivatives, which have been developed in relatively recent years, are summarized. Such procedures should provide a new practical methodology to synthesize the desired aldehyde products in high yields.

항염작용이 기대되는 새로운 피롤리딘닐 1,2-벤조티아진 유도체의 합성 (Synthesis of Antiinflammatory Novel 3-Pyrrolidinyl 1,2-Benzothiazine Derivatives)

  • 박명숙
    • 약학회지
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    • 제41권6호
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    • pp.724-729
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    • 1997
  • New 7-Halo-4-hydroxy-2-allyl-N-3-(4-methoxy-2-carboxylic acid pyrrolidinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide derivatives were synthesized through the condensation of 7-halo-4-hydroxy-2-allyl-1,2-benzothiazine-3-carboxylic acid methyl ester 1,1-dioxide with 4-methoxy L-proline.

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