(1S,4S)-5-(phenylsulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one | 1349197-85-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,4S)-5-(phenylsulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one
• 英文别名: (1S,4S)-5-(benzenesulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one
• CAS: 1349197-85-8
• 化学式: C₁₁H₁₁NO₄S
• 分子量: 253.279
• InChiKey: QXPHHVLVLMONQB-WPRPVWTQSA-N

物化性质

• 沸点：
  485.8±55.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4S)-5-(phenylsulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 (2S)-2-((2S,4R)-4-(4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)-propyl)carbamoyl)-1H-1,2,3-triazol-1-yl)-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid
  参考文献：
  名称：

  Design, synthesis and binding properties of a fluorescent α₉β₁/α₄β₁integrin antagonist and its application as anin vivoprobe for bone marrow haemopoietic stem cells

  摘要：

  一种具有纳摇结合亲和力的荧光α9β1整合素拮抗剂已被证明能够结合骨髓造血干细胞和祖细胞体内。

  DOI：

  10.1039/c3ob42332h
• 作为产物：
  描述：

  苯磺酰氯 在 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (1S,4S)-5-(phenylsulfonyl)-2-oxa-5-azabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Studies on the Synthesis of cis-4-Hydroxy-L-proline

  摘要：

  我们开发出了一种高产的三步实用程序，该程序依赖于萃取加工程序，通过三个步骤将 N-苯磺酰基-反式-4-羟基-l-脯氨酸转化为 N-苯磺酰基-顺式-4-羟基-l-脯氨酸甲酯，收率高达 82%。

  DOI：

  10.1071/ch11204

文献信息

• DISLODGEMENT AND RELEASE OF HSC FROM THE BONE MARROW STEM CELL NICHE USING ALPHA9 INTEGRIN ANTAGONISTS
  申请人：COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION

  公开号：US20170348375A1

  公开（公告）日：2017-12-07

  Haematopoietic stem cell mobilization is a process whereby haematopoietic stem cells are stimulated out of the bone marrow space. Before HSC can mobilize, they must be dislodged and released from the BM stem cell niche in which they reside and are retained by adhesive interactions. Accordingly, in an aspect of the present invention there is provided a method for enhancing dislodgement of HSC and their precursors and progenitors thereof from a BM stem cell binding ligand in vivo or ex vivo, said method comprising administering in vivo or ex vivo an effective amount of an antagonist of an a 9 integrin or an active portion thereof to the BM stem cell niche. Once mobilized to the peripheral blood (PB) the HSC may be collected for transplant. Methods which enhance mobilization of the HSC can also improve treatments of haematological disorders.
• [EN] DISLODGEMENT AND RELEASE OF HSC FROM THE BONE MARROW STEM CELL NICHE USING ALPHA9 INTEGRIN ANTAGONISTS<br/>[FR] DÉTACHEMENT ET LIBÉRATION DE CELLULES SOUCHES HÉMATOPOÏÉTIQUES À PARTIR DE NICHE DE CELLULES SOUCHES DE MOELLE OSSEUSE AU MOYEN D'ANTAGONISTES D'INTÉGRINE ALPHA-9
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2016090403A1

  公开（公告）日：2016-06-16

  Haematopoietic stem cell mobilization is a process whereby haematopoietic stem cells are stimulated out of the bone marrow space. Before HSC can mobilize, they must be dislodged and released from the BM stem cell niche in which they reside and are retained by adhesive interactions. Accordingly, in an aspect of the present invention there is provided a method for enhancing dislodgement of HSC and their precursors and progenitors thereof from a BM stem cell binding ligand in vivo or ex vivo, said method comprising administering in vivo or ex vivo an effective amount of an antagonist of an α 9 integrin or an active portion thereof to the BM stem cell niche. Once mobilized to the peripheral blood (PB) the HSC may be collected for transplant. Methods which enhance mobilization of the HSC can also improve treatments of haematological disorders.
• Design, synthesis and binding properties of a fluorescent α₉β₁/α₄β₁integrin antagonist and its application as an<i>in vivo</i>probe for bone marrow haemopoietic stem cells
  作者：Benjamin Cao、Oliver E. Hutt、Zhen Zhang、Songhui Li、Shen Y. Heazlewood、Brenda Williams、Jessica A. Smith、David N. Haylock、G. Paul Savage、Susan K. Nilsson

  DOI：10.1039/c3ob42332h

  日期：——

  A fluorescent α₉β₁integrin antagonist with nanomolar binding affinities has been demonstrated to bind bone marrow haemopoietic stem and progenitor cellsin vivo.

  一种具有纳摇结合亲和力的荧光α9β1整合素拮抗剂已被证明能够结合骨髓造血干细胞和祖细胞体内。
• Studies on the Synthesis of cis-4-Hydroxy-L-proline
  作者：Jessica A. Smith、G. Paul Savage、Oliver E. Hutt

  DOI：10.1071/ch11204

  日期：——

  A high yielding practical three-step procedure, which relies on an extractive work-up procedure, has been developed to convert N-phenylsulfonyl-trans-4-hydroxy-l-proline to N-phenylsulfonyl-cis-4-hydroxy-l-proline methyl ester in 82 % yield over three steps.

  我们开发出了一种高产的三步实用程序，该程序依赖于萃取加工程序，通过三个步骤将 N-苯磺酰基-反式-4-羟基-l-脯氨酸转化为 N-苯磺酰基-顺式-4-羟基-l-脯氨酸甲酯，收率高达 82%。