2-Hydroxy-2-(L-pyrrolidin-2-yl)acetic acid | 72351-44-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-Hydroxy-2-(L-pyrrolidin-2-yl)acetic acid
• 英文别名: 2-hydroxy-2-(pyrrolidin-2-yl)acetic acid；(R,S)-2-Hydroxy-2-(L-pyrrolidin-2-yl)acetic acid；2-hydroxy-2-pyrrolidin-2-ylacetic acid
• CAS: 72351-44-1
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: SKBCRDTZCCZJRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-(L-pyrrolidin-2-yl)acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [2-hydroxy-2-(N-benzyloxycarbonyl-pyrrolidin-2-yl)acetyl]-D-leucine t-butyl ester
  参考文献：
  名称：

  Poststatin, a New Inhibitor of Prolyl Endopeptidase. VI. Endopeptidase Inhibitory Activity of Poststatin Analogues Containing Pyrrolidine Ring.

  摘要：

  合成了几种含有吡咯烷结构片段的波斯他丁类似物，并研究了它们对脯氨酰内肽酶和组织蛋白酶B的体外抑制活性。将波斯他丁中的波斯汀残基替换为2-氧代-2-(2-吡咯烷基)乙酸，增加了其对脯氨酰内肽酶的选择性和抑制活性。苄氧羰基-L-苯丙氨酰-(S)-2-氧代-2-(2-吡咯烷基)乙酰基-D-苯丙氨酸对脯氨酰内肽酶的活性约为天然波斯他丁的46倍。

  DOI：

  10.7164/antibiotics.49.900
• 作为产物：
  描述：

  N-CBZ-吡咯烷-2-甲醛 在 盐酸 、 sodium metabisulfite 、 Dowex₅₀W-X₄ 、 氢气 作用下， 反应 10.5h， 生成 2-Hydroxy-2-(L-pyrrolidin-2-yl)acetic acid
  参考文献：
  名称：

  Poststatin, a New Inhibitor of Prolyl Endopeptidase. VI. Endopeptidase Inhibitory Activity of Poststatin Analogues Containing Pyrrolidine Ring.

  摘要：

  合成了几种含有吡咯烷结构片段的波斯他丁类似物，并研究了它们对脯氨酰内肽酶和组织蛋白酶B的体外抑制活性。将波斯他丁中的波斯汀残基替换为2-氧代-2-(2-吡咯烷基)乙酸，增加了其对脯氨酰内肽酶的选择性和抑制活性。苄氧羰基-L-苯丙氨酰-(S)-2-氧代-2-(2-吡咯烷基)乙酰基-D-苯丙氨酸对脯氨酰内肽酶的活性约为天然波斯他丁的46倍。

  DOI：

  10.7164/antibiotics.49.900

文献信息

• .alpha.-keto amide derivatives
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US05221752A1

  公开（公告）日：1993-06-22

  The present invention discloses a new .alpha.-keto amide derivative or a salt thereof represented by the formula (1): ##STR1## wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C.sub.n H.sub.2n-1) and is a halogen, lower alkoxy or hydrogen, A represents a carbonyl group or mono- or di-substituted methylene (the substituent being a hydroxy, lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6. The compound of the present invention is effective in inhibiting prolyl endopeptidase activity and useful as an active ingredient of an enzyme inhibitor.

  本发明公开了一种新的α-酮酰胺衍生物或其盐，其由以下式表示：其中X代表（1）可能被保护的肽残基或氨基酸残基，（2）氢原子或（3）氨基保护基，Y代表可能被保护的肽残基或氨基酸残基，E代表烷基（CnH2n-1）上的取代基，可以是卤素、低烷氧基或氢，A代表羰基或单取代或双取代的亚甲基（取代基为羟基、低烷氧基、苯亚胺基或苄亚胺基），n代表2至6的整数。本发明的化合物在抑制脯氨酸内肽酶活性方面具有有效性，并可用作酶抑制剂的活性成分。
• Pyrrolidine derivatives having inhibitory action for proline specific
  申请人：Sumitomo Pharmaceuticals Company, Ltd.

  公开号：US04880827A1

  公开（公告）日：1989-11-14

  Pyrrolidine derivatives having inhibitory action for proline-specific endopeptidase which are useful for anti-amnestic agent. The disclosed pyrrolidine derivatives as well as their acid addition salts can be administered orally or parenterally in the form of conventional pharmaceutical preparations. For instance, they can be administered orally in the form of conventional solid pharmaceutical preparations such as tablets, capsules, syrups and suspensions. Alternatively, they can be administered parenterally by injection in the form of conventional liquid pharmaceutical preparations such as solutions, emulsions, suspensions, etc. Also, they may be directly applied to rectum in the form of suppository. Further, the preparations may contain physiologically acceptable carriers, excipients, activators, binding agents, stabilizers, etc. In the case of injections, physiologically acceptable buffers, solubilizing agents or isotonic agents may be incorporated therein. Methods of production are also disclosed.

  吡咯烷衍生物具有对脯氨酸特异性内切肽酶的抑制作用，可用作抗遗忘剂。公开的吡咯烷衍生物及其酸盐可以以常规药物制剂的形式经口或经肌肉注射给药。例如，它们可以以片剂、胶囊、糖浆和悬浮剂等常规固体药物制剂的形式经口给药。另外，它们可以以溶液、乳剂、悬浮剂等常规液体药物制剂的形式经肌肉注射给药。此外，它们也可以直接以栓剂的形式直肠应用。制剂可能含有生理上可接受的载体、赋形剂、活性剂、结合剂、稳定剂等。在注射剂中，可能会加入生理上可接受的缓冲剂、溶解剂或等渗剂。此外，还公开了生产方法。
• Novel aminoglycoside derivatives
  申请人：Shionogi & Co., Ltd.

  公开号：US04200628A1

  公开（公告）日：1980-04-29

  Novel aminoglycoside derivatives and their salts containing 2-deoxystreptamine moiety, of which the 1-amino group is acylated by a group represented by the formula: ##STR1## (wherein R is 4 to 6 membered heterocyclic group containing 1 to 2 nitrogen atoms which may optionally be substituted.) effective in treatment of infectious diseases caused by gram positive and gram negative bacteria.

  含有2-脱氧链霉素结构单元的新型氨基糖苷衍生物及其盐，其中1-氨基团被表示为以下式的基团酰化：##STR1##（其中R是含有1到2个氮原子的4到6元杂环基团，可选择性地被取代）。对治疗由革兰氏阳性和革兰氏阴性细菌引起的传染病有效。
• Aminoglycoside derivatives, process for their manufacture, pharmaceutical compositions and carboxylic acids
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0001643A2

  公开（公告）日：1979-05-02

  Aminoglycoside derivatives of the general formula (I) wherein R is an optionally substituted 4- to 6-membered heterocyclic group containing 1 or 2 nitrogen atoms; R is aminomethyl, hydroxymethyl, 1-aminoethyl, or 1-methylaminoethyl; R', R and R" are each hydrogen or hydroxy; π2 R3 and R° are each hydrogen or hydroxy; R4 is hydroxy or amino; R5 is amino or methylamino; R' is hydroxy or methyl; R" is hydrogen, hydroxymethyl, or carbamoyloxymetnyl; and the dotted line represents the optional presence of a double bond and their salts with acids, a process for their manufacture, pharmaceutical compositions having antibiotic activity and containing compounds of the general formula (I); furthermore carboxylic acids of the general formula (III) wherein R has the above meaning, useful as intermediates for preparing the compounds of the general formula (I).

  通式(I)的氨基糖苷衍生物 其中 R 是任选取代的含有 1 或 2 个氮原子的 4 至 6 元杂环基团； R 是氨甲基、羟甲基、1-氨基乙基或 1-甲基氨基乙基； R'、R 和 R" 均为氢或羟基； π2 R3 和 R° 均为氢或羟基； R4 是羟基或氨基 R5 是氨基或甲氨基 R' 是羟基或甲基； R" 是氢、羟甲基或氨基甲酰氧甲基；以及 虚线表示可选择存在的双键 及其与酸的盐类、其制造方法、具有抗生素活性并含有通式（I）化合物的药物组合物；以及通式（III）的羧酸 其中 R 具有上述含义，可用作制备通式（I）化合物的中间体。
• Pyrrolidine derivatives
  申请人：SUMITOMO PHARMACEUTICALS COMPANY, LIMITED

  公开号：EP0238319A1

  公开（公告）日：1987-09-23

  Pyrrolidine derivatives which have inhibitory action for proline-specific endopeptidase and are useful as anti-amnesic agents, have the formula: wherein R1 R3, R4, and R5 are each independently hydrogen, hydroxy, halogen, lower alkyl, phenyl, substituted phenyl, -CH2R14, -X-R15, or in which R14 is phenyl or substituted phenyl. X is oxygen atom or sulfur atom. R15 is lower alkyl, phenyl or substituted phenyl or -CH2R20 (in which R20 is phenyl or substituted phenyl). R16 is lower alkyl, phenyl, substituted phenyl or -CH2R21 (in which R21 is phenyl or substituted phenyl). R17 is lower alkyl, five or six-membered cycloalkyl, phenyl, substituted phenyl, -CH2R22 (in which R22 is phenyl or substituted phenyl) (in which R23 is lower alkyl, phenyl or substituted phenyl). R18 and R19 are each independently lower alkyl or -CH2R24 (in which R24 is phenyl or subsubstituted phenyl)}. R6 is hydrogen or lower alkyl. R7 is hydrogen, lower alkyl, benzyl, or -(CH2)n-R25 in which n is an integer of 0 to 4. R25 is -OH, -SH, -NH2, -SCH3, heterocyclic group, or -C02R26 (in which R26 is hydrogen or lower alkyl or benzyl)}. R8 is hydrogen or, when R8 and R7 are taken together with the adjacent nitrogen atom and carbon atom to which they are attached, they represent five-membered heterocyclic group. R9 is hydrogen, lower alkyl, phenyl, substituted phenyl. R10 is hydrogen, lower alkyl, lower alkoxy or halogen. m is an integer of 0 to 3. R11 is hydrogen, lower alkyl, phenyl, substituted phenyl or-CH2R27 (in which R27 is phenyl or substituted phenyl). R12 is lower alkyl or, when R12 and R12 are each taken together, they represent lower alkylene. R13 is lower alkyl, phenyl, substituted phenyl or CH2R28 (in which R28 is phenyl or substituted phenyl) and their production and use.

  吡咯烷衍生物对脯氨酸特异性内肽酶有抑制作用，可用作抗氨化剂，其分子式为 其中 R1 R3、R4 和 R5 各自独立地为氢、羟基、卤素、低级烷基、苯基、取代苯基、-CH2R14、-X-R15、 或 其中 R14 是苯基或取代苯基。X 是氧原子或硫原子。R15 是低级烷基、苯基或取代苯基或-CH2R20（其中 R20 是苯基或取代苯基）。R16 是低级烷基、苯基、取代苯基或 -CH2R21（其中 R21 是苯基或取代苯基）。R17 是低级烷基、五或六元环烷基、苯基、取代苯基、-CH2R22（其中 R22 是苯基或取代苯基）。 (其中 R23 为低级烷基、苯基或取代苯基）。R18 和 R19 各自独立地为低级烷基或-CH2R24（其中 R24 为苯基或亚取代苯基）}。R6 是氢或低级烷基。R7 是氢、低级烷基、苄基、 或-(CH2)n-R25 其中 n 为 0 至 4 的整数。R25 是-OH、-SH、-NH2、-SCH3、 杂环基团，或-C02R26（其中 R26 为氢或低级烷基或苄基）}。R8 是氢，或者当 R8 和 R7 与相邻的氮原子和碳原子相连时，它们代表五元杂环基团。R9 是氢、低级烷基、苯基、取代苯基。R10 是氢、低级烷基、低级烷氧基或卤素。R11 是氢、低级烷基、苯基、取代苯基或-CH2R27（其中 R27 是苯基或取代苯基）。R12 是低级烷基，或者当 R12 和 R12 各自合在一起时，它们代表低级亚烷基。R13 是低级烷基、苯基、取代苯基或 CH2R28（其中 R28 是苯基或取代苯基）及其生产和使用。