(3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one | 75666-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one
• 英文别名: (2S-trans)-2-(acetyloxy)-4-oxo-3-azetidinecarbamic acid phenylmethyl ester；trans-4-acetoxy-3-benzyloxycarbonylamino-2-azetidinone；(3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-one；[(2S,3S)-4-oxo-3-(phenylmethoxycarbonylamino)azetidin-2-yl] acetate
• CAS: 75666-47-6
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: UIXSASZBPZYESC-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one 生成 potassium;2-acetyloxy-4-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-sulfonate
  参考文献：
  名称：

  BREUER, H.;DENZEL, T.

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (3S,5R,6R)-6-benzyloxycarbonylamino-2,2-dimethylpenam-3-carboxylate 在 potassium permanganate 、 mercury(II) diacetate 作用下， 以 丙酮 为溶剂， 反应 0.75h， 生成 (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one
  参考文献：
  名称：

  Synthesis and antibacterial activity of C4 substituted monobactams

  摘要：

  The synthesis and antibacterial activity of a series of monobactams having various substituents at C4 position is described. An efficient route to versatile intermediates 4a-c from 6-aminopenicillanic acid (6-APA) has been developed. Derivatives 10e, 11, 21 showed good to moderate activity against Gram-negative bacteria with the exception of Pseudomonas aeruginosa. Introduction of a catechol moiety on the C4 side chain only slightly improved the activity against P aeruginosa.

  DOI：

  10.1016/0223-5234(92)90101-6

文献信息

• 4-substitued-3-[1 or 2 amino acid residue]-azetidin-2-one derivatives
  申请人：Synphar Laboratories, Inc.

  公开号：US05986108A1

  公开（公告）日：1999-11-16

  Disclosed herein are azetidin-2-one compounds which exhibit excellent cysteine proteinase inhibitory activity. The compounds are 4-substituted-3-1 or 2 amino acid residue}-azetidin-2-ones of forumula I ##STR1## wherein AAR is a 1 or 2 acid residue, and R.sub.1 and R.sub.2 are as defined herein. The compounds can be used in the treatment of various diseases such as muscular dystrophy, bone resorption disorders, myocardial infarction and cancer metastasis.

  本发明公开了具有优异半胱氨酸蛋白酶抑制活性的氮杂环丁-2-酮化合物。这些化合物是4-取代-3-1或2个氨基酸残基}-氮杂环丁-2-酮，其通式为I ##STR1##其中AAR表示1或2个氨基酸残基，R1和R2如本文所定义。这些化合物可用于治疗各种疾病，如肌肉萎缩症、骨质吸收障碍、心肌梗死和癌症转移。
• 6-substituted amino-4-oxa-1-azabicyclo \x9b3,2,0! heptan-7-one derivatives
  申请人：National Research Council of Canada

  公开号：US05905076A1

  公开（公告）日：1999-05-18

  Novel 6-substituted amino-4-oxa-1-azabicyclo\x9b3,2,0!heptan-7-one compounds, as well as the pharmaceutically acceptable salts thereof and diastereoisomers thereof, of formula I, ##STR1## are disclosed, which exhibit excellent cysteine protease inhibitory activity and may be used for treatment of different diseases such as muscular dystrophy, arthritis, myocardial infarction, Alzheimer's disease, bacterial infection, common cold, osteroporosis and cancer metastasis.

  新型6-取代氨基-4-氧-1-氮杂双环[3,2,0]庚烷-7-酮化合物，以及其药用可接受的盐和对映异构体，化学式I，##STR1## 被披露，这些化合物表现出优秀的半胱氨酸蛋白酶抑制活性，并可用于治疗不同疾病，如肌肉萎缩症、关节炎、心肌梗死、阿尔茨海默病、细菌感染、感冒、骨质疏松症和癌转移。
• Design and synthesis of 6-substituted amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one derivatives as cysteine proteases inhibitors
  作者：Nian E Zhou、Deqi Guo、Jadwiga Kaleta、Enrico Purisima、Robert Menard、Ronald G Micetich、Rajeshwar Singh

  DOI：10.1016/s0960-894x(02)00765-5

  日期：2002.12

  A series of 6-substituted amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one compounds was designed and synthesized as a new class of inhibitors for cysteine proteases cathepsins B, L, K, and S. One compound (5S,6S)-6-(N-benzyloxycarbonyl-L-phenylalanyl) amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one showed excellent cathepsin L and K inhibition activity with IC(50) at a low nanomolar range.

  设计并合成了一系列6-取代的氨基-4-氧杂-1-氮杂双环[3,2,0]庚-7-酮化合物，作为半胱氨酸蛋白酶组织蛋白酶B，L，K和S的新型抑制剂。一种化合物（5S，6S）-6-（N-苄氧基羰基-L-苯丙氨酰基）氨基-4-氧杂-1-氮杂双环[3,2,0]庚-7-酮具有出色的组织蛋白酶L和K抑制活性低纳摩尔范围的IC（50）。
• Reduction process for the preparation of 4-unsubstituted azetidin-2-ones
  申请人：——

  公开号：US04683303A1

  公开（公告）日：1987-07-28

  Novel process for the preparation of azetidin-2-ones of the formula ##STR1## wherein R.sup.1 and R.sup.2 independently from each other are hydrogen, or an organic group linked to the ring carbon via a carbon atom, a nitrogen atom or an oxygen atom, characterized in that a corresponding 4-acyloxyazetidin-2-one, which is substituted by a group --O--CO--R.sup.3 at the 4-position, wherein R.sup.3 is hydrogen or an organic radical stable at the reaction conditions, is reacted with a complex metal hydride comprising reactive hydride ions, such as, lithium borohydride, sodium borohydride, potassium borohydride, zinc borohydride or tetraorganoammonium borohydride.

  制备azetidin-2-酮的新方法，其化学式为##STR1##其中R.sup.1和R.sup.2独立地是氢，或通过碳原子、氮原子或氧原子与环碳相连的有机基团，其特征在于，将相应的4-酰氧基azetidin-2-酮与在4位被一个--O--CO--R.sup.3基团取代的基团反应，其中R.sup.3是在反应条件下稳定的氢或有机基团，所用的试剂是包含反应性氢化物离子的复杂金属氢化物，如硼氢化锂、硼氢化钠、硼氢化钾、硼氢化锌或四有机铵硼氢化物。
• β-Lactams from ester enolates and silylimines: An enantiospecific synthesis of monocyclic β-lactams.
  作者：Patrizia Andreoli、Laura Billi、Gianfranco Cainelli、Mauro Panunzio、Elisa Bandini、Giorgio Martelli、Giuseppe Spunta

  DOI：10.1016/s0040-4020(01)86509-1

  日期：1991.11

  oxidation led to the optically active (3S, 4S ) 3-amino-4-acetoxy-β-laclam. The absolute configuration of this compound was determined by elaboration of this substrate to a key intermediate in the synthesis of the antibiotic “Aztreonam”. Nucleophilic displacement of the acetoxy group led to optically active 3-amino-4-alkyl (aryl)-azetidin-2-ones.

  光学活性的3,4-二取代的氮杂环丁烷-2-酮已通过将（S）或（R）-丙醛衍生的手性甲硅烷基苯胺与2,2,5,5，-四甲基-1乙酯的烯醇酯脱核而制得1,2,5-氮杂二硅氮杂环丁烷-1-乙酸盐（STABASE）。β-内酰胺环的C-4位置上的羟乙基侧链氧化，然后进行Baeyer-Villiger氧化，产生旋光性（3S，4S）3-氨基-4-乙酰氧基-β-内酰胺。该化合物的绝对构型是通过将底物精加工成抗生素“氨曲南”合成中的关键中间体来确定的。乙酰氧基的亲核取代导致光学活性的3-氨基-4-烷基（芳基）-氮杂环丁烷-2-酮。