関: mesylate、methanesulfonate

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/24 01:42:47」(JST)

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Structural formula of the mesylate anion

Ball-and-stick model of the mesylate anion

In chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH₃SO₃H). In salts, the mesylate is present as the CH₃SO₃⁻ anion. When modifying the International Nonproprietary Name of a pharmaceutical substance containing the group or anion, the correct spelling is mesilate (as in imatinib mesilate, the mesylate salt of imatinib).^[1]

Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH₃SO₂O–R, abbreviated MsO–R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions.

Preparation

Mesylates are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine.^[2]

Mesyl

Related to mesylate, is the mesyl, an abbreviation for methanesulfonyl or CH₃SO₂ (Ms) functional group. For example, methanesulfonyl chloride is often referred to as mesyl chloride. Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitrogen are robust with respect to hydrolysis.^[3] This functional group appears in a variety of medications, particularly cardiac (i.e. “antiarrhythmic”) but as sulfonamide moiety. Examples include Sotalol, ibutilide, sematilide, Dronedarone, Dofetilide, E-4031, and Bitopertin .

References

^ World Health Organization (February 2006). "International Nonproprietary Names Modified" (PDF). INN Working Document 05.167/3. WHO. Retrieved 5 December 2008.
^ Rick L. Danheiser, Yeun-Min Tsai, and David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Org. Synth. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates).
^ Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2

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「メシル酸塩」

　　[★]

英: mesylate、mesilate、methanesulfonate
関: メシレート、メタンスルホン酸、メタンスルホン酸塩、メシル酸

「methanesulfonate」

　　[★]

メタンスルホン酸、メシル酸塩、メタンスルホン酸塩

関: mesilate、mesylate、methanesulfonic acid

「メタンスルホン酸塩」

　　[★]

英: methanesulfonate、mesilate
関: メシル酸塩、メシレート、メタンスルホン酸、メシル酸

「メシル酸」

　　[★]

英: mesylate、mesilate
関: メシル酸塩、メシレート、メタンスルホン酸塩

「mesylate」

　　[★]

メシル酸、メシル酸塩、メシレート

関: mesilate、methanesulfonate

「thioproperazine mesilate」

　　[★]

メシル酸チオプロペラジン

関: thioproperazine

「nelfinavir mesilate」

　　[★]

メシル酸ネルフィナビル

関: nelfinavir

「pergolide mesilate」

　　[★]

メシル酸ペルゴリド

関: pergolide

[1] World Health Organization (February 2006). "International Nonproprietary Names Modified" (PDF). INN Working Document 05.167/3. WHO. Retrieved 5 December 2008.

[2] Rick L. Danheiser, Yeun-Min Tsai, and David M. Fink (1966). "A General Method for the Synthesis of Allenylsilanes: 1-Methyl-1-(trimethylsilyl)allene". Org. Synth. doi:10.15227/orgsyn.066.0001. (a procedure illustrating the use of mesylates).

[3] Valerie Vaillancourt, Michele M. Cudahy, Matthew M. Kreilein and Danielle L. Jacobs "Methanesulfonyl Chloride" in E-EROS Encyclopedia for Reagents in Organic Synthesis. doi:10.1002/047084289X.rm070.pub2

リンク元	「メシル酸塩」「methanesulfonate」「メタンスルホン酸塩」「メシル酸」「mesylate」
拡張検索	「thioproperazine mesilate」「nelfinavir mesilate」「pergolide mesilate」

匿名

検索

案内

案内

mesilate