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Updated: Jul 9, 2026
13:37
Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
サリノスポラミドAの単純なステレオ制御合成です
Leleti Rajender Reddy1, P Saravanan, E J Corey
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Journal of the American Chemical Society
|May 20, 2004
まとめ
サリノスポラミドAの新しい合成が開発され,研究のためにかなりの量を提供しました. この画期的な発見により,様々な腫瘍細胞系に対する強力な抗癌特性についてのさらなる研究が可能になりました.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 薬用化学 薬用化学について
- がん生物学 がん生物学
背景:
- サリノスポラミドAは,多数の腫瘍細胞系に対して,強力な in vitro 細胞毒性活性を示しています.
- この化合物の重要な抗癌能力は,信頼性の高いスケーラブルな合成方法を必要とします.
- 以前の合成経路は,実質的な収穫量や単純性のために最適化されていなかった.
研究 の 目的:
- サリノスポラミドAのシンプルで効果的なステレオ制御合成を開発する.
- 生物学的評価をさらに進めるため,大量にサリノスポラミドAを生産する.
- サリノスポラミドAの抗癌メカニズムに関する研究を促進する.
主な方法:
- 新しいステレオ制御された合成経路が設計され,実行されました.
- 効率と収量のために反応条件の最適化.
- 合成されたサリノスポラミドAの浄化と特徴付け.
主要な成果:
- サリノスポラミドAの直接的かつステレオ選択的合成が成功裏に確立されました.
- 開発された方法は,大量にサリノスポラミドA.を生産する.
- 合成された化合物は,様々ながん細胞系に対して強力な細胞毒性活性 (IC50 ≤ 10 nM) を保持しています.
結論:
- サリノスポラミドAの最初の成功合成は,この化合物の有意な量を得るための実行可能な経路を提供します.
- このスケーラブルな合成により,腫瘍学におけるサリノスポラミドAの治療の可能性を調査する生物学的研究が加速されます.
- この方法によるサリノスポラミドAの利用可能性は,薬剤開発とがん研究のための新しい道を開く.
関連する概念動画
02:54Ions as Acids and Bases
Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
04:08Determining the pH of Salt Solutions
The pH of a salt solution is determined by its component anions and cations. Salts that contain pH-neutral anions and the hydronium ion-producing cations form a solution with a pH less than 7. For example, in ammonium nitrate (NH4NO3) solution, NO3− ions do not react with water whereas NH4+ ions produce the hydronium ions resulting in the acidic solution. In contrast, salts that contain pH-neutral cations and the hydroxide ion-producing anions form a solution with a pH greater than 7. For...
02:16Brønsted-Lowry Acids and Bases
In 1923, the Brønsted–Lowry definition of acids and bases was proposed by Johannes Brønsted and Thomas Lowry. According to this theory, a Brønsted acid is defined as a species that donates a proton in a chemical reaction and gets converted to its conjugate base. A Brønsted base is defined as a species that accepts a proton in a chemical reaction and gets converted into its conjugate acid. These transfers of protons are caused by the displacement of electrons in these reactions, which is...
01:07Acid Halides to Amides: Aminolysis
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
01:29Preparation of Amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
01:19Structure of Amines
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...