2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate | 162360-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate
• 英文别名: [2-Acetamido-2-(acetyloxymethyl)-4-(4-hydroxyphenyl)butyl] acetate
• CAS: 162360-77-2
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: XKEHMWVPWAMNJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate 在 caesium carbonate 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-amino-2-(4-propoxyphenethyl)propane-1,3-diol hydrochloride
  参考文献：
  名称：

  Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

  摘要：

  BITE生物等构替代物Et和CF3允许在多发性硬化药物吉列尼亚的类似物中调节亲脂性。

  DOI：

  10.1039/c8cc05643a
• 作为产物：
  描述：

  1-乙烯基-4-苯基甲氧基苯 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 palladium on activated carbon 、 氢气 、 碘 、 sodium hydride 、 三乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 173.5h， 生成 2-acetamido-2-(4-hydroxyphenethyl)-propane-1,3-diyl diacetate
  参考文献：
  名称：

  Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

  摘要：

  BITE生物等构替代物Et和CF3允许在多发性硬化药物吉列尼亚的类似物中调节亲脂性。

  DOI：

  10.1039/c8cc05643a

文献信息

• Stereocontrolled Synthesis of Tetrafluoropentanols: Multivicinal Fluorinated Alkane Units for Drug Discovery
  作者：Patrick Bentler、Nathalie Erdeljac、Kathrin Bussmann、Marie Ahlqvist、Laurent Knerr、Klaus Bergander、Constantin G. Daniliuc、Ryan Gilmour

  DOI：10.1021/acs.orglett.9b02662

  日期：2019.10.4

  A stereodivergent synthesis of four diastereomeric 2,3,4,5-tetrafluoropentanols is disclosed. X-ray crystallographic analysis reveals conformations that manifest sequential stereoelectronic gauche effects (σC–H/C → σC–F*), thereby generating topological diversity via subtle C(sp3)–H to C(sp3)–F exchange. Two representative tetrafluoro arrays have been incorporated into truncated analogues of Gilenya

  公开了四种非对映异构的2,3,4,5-四氟戊醇的立体发散合成。X射线晶体分析揭示构象该清单的顺序立体电子笨拙效应（σ C-H / C →σ C-F *），从而通过微妙Ç生成拓扑多样性（SP 3）-H至C（SP 3）-F交换。两个代表性的四氟阵列已被纳入Gilenya的截短类似物中，用于复发性多发性硬化的管理。这些紧密相似的多邻位氟代烷烃具有明显不同的理化特性，并且在存在人微粒体的情况下是稳定的。
• 2-AMINO-1,3-PROPANEDIOL COMPOUND AND IMMUNOSUPPRESSANT
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0627406A1

  公开（公告）日：1994-12-07

  A 2-amino-1,3-propanediol compound represented by general formula (I) or a pharmaceutically acceptable salt thereof, and an immunosuppressant containing the same as the active ingredient. In said formula R represents optionally substituted linear or branched carbon chain, optionally substituted aryl or optionally substituted cycloalkyl; and R2, R3, R4 and R5, which may be the same or different from one another, represent each hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl. The compound is immunodepressant and useful as an inhibitor against rejection in organ or bone marrow transplantation, as a preventive or remedy for autoimmune diseases and so forth, or a reagent in the medical and pharmaceutical fields.

  一种由通式(I)代表的2-氨基-1,3-丙二醇化合物或其药学上可接受的盐，以及一种以其为活性成分的免疫抑制剂。在所述式中，R 代表任选取代的直链或支链碳链、任选取代的芳基或任选取代的环烷基；而 R2、R3、R4 和 R5（它们彼此可以相同或不同）分别代表氢、烷基、芳烷基、酰基或烷氧基羰基。该化合物具有免疫抑制作用，可作为器官移植或骨髓移植中的排斥抑制剂、自身免疫性疾病的预防或治疗药物等，也可作为医疗和制药领域的试剂。
• TX-2152: A conformationally rigid and electron-rich diyne analogue of FTY720 with in vivo antiangiogenic activity
  作者：Shinichi Nakayama、Yoshihiro Uto、Kanako Tanimoto、Yasuhiro Okuno、Yuki Sasaki、Hideko Nagasawa、Eiji Nakata、Ken Arai、Kaori Momose、Tetsuro Fujita、Toshihiro Hashimoto、Yasuko Okamoto、Yoshinori Asakawa、Satoru Goto、Hitoshi Hori

  DOI：10.1016/j.bmc.2008.07.003

  日期：2008.8

  We designed FTY720 analogues with conformationally rigid and electron-rich acetylenic chains as anti-angiogenic agents ( the monoyne 1: TX-2148, the diyne 2: TX-2152, the triyne 3: TX-2256). Molecular orbital ( MO) calculations of our designed acetylenic analogues and FTY720 showed that the localization of the lowest unoccupied MO and the highest occupied MO increased from phenyl ring to acetylenic chain compared with that of FTY720. These acetylenic analogues were synthesized from p-hydroxyphenylethanol as a starting material. The construction of the acetylenic chain was carried out by an iterative strategy using a Sonogashira cross-coupling reaction and desilylative bromination in two steps. The corresponding overall yields of the monoyne 1, the diyne 2, and the triyne 3 were 27% ( 11 steps), 13% ( 13 steps), and 10% ( 15 steps). The in vivo antiangiogenic activities of these acetylenic analogues and FTY720 were evaluated by the chick embryo chorioallantoic membrane ( CAM) assay and compared to the activities of the known antiangiogenic agent TNP-470. The diyne 2 showed more potent antiangiogenic activity ( 90% inhibition) than FTY720 ( 77% inhibition) and other acetylenic analogues ( the monoyne 1: 42% inhibition, the triyne 3: 60% inhibition), and TNP-470 ( 82% inhibition) at a dose of 10 mu g/CAM, without showing toxicity. The diyne 2 also had potent inhibitory activity at a dose of 5 and 2.5 mu g/CAM. These results indicate that the flexibility of C8 alkyl chain of FTY720 is not required for its antiangiogenic activity. We suggest that the diyne 2 ( TX-2152) may be a promising candidate as an antiangiogenic agent for antineoplastic drug discovery. (C) 2008 Elsevier Ltd. All rights reserved.
• EP0627406B1
  申请人：——

  公开号：EP0627406B1

  公开（公告）日：1998-10-28
• US5604229A
  申请人：——

  公开号：US5604229A

  公开（公告）日：1997-02-18