methyl 2-(N-2-methyl-4-hydroxy-2-butenyl)amino benzoate | 878143-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(N-2-methyl-4-hydroxy-2-butenyl)amino benzoate
• 英文别名: methyl 2-(N-2-methyl-4-hydroxy-2-butenyl)aminobenzoate；methyl 2-[[(E)-4-hydroxy-2-methylbut-2-enyl]amino]benzoate
• CAS: 878143-08-9
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: KKNBINKCUSTHPI-JXMROGBWSA-N

物化性质

• 沸点：
  394.1±32.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-2-methyl-4-hydroxy-2-butenyl)amino benzoate 在 15-冠醚-5 、 sodium hydride 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 dimethyl 2,2'-(((2E,7E)-5,5-bis(diethoxyphosphoryl)-2,8-dimethylnona-2,7-diene-1,9-diyl)bis(azanediyl))dibenzoate
  参考文献：
  名称：

  Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation

  摘要：

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.002
• 作为产物：
  描述：

  梨醇酯 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 selenium(IV) oxide 、 4 A molecular sieve 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 溶剂黄146 、 对羟基苯甲酸 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 52.5h， 生成 methyl 2-(N-2-methyl-4-hydroxy-2-butenyl)amino benzoate
  参考文献：
  名称：

  Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation

  摘要：

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.002

文献信息

• Geranylgeranyl pyrophosphate synthase inhibitors
  申请人：Wiemer F. David

  公开号：US20060052347A1

  公开（公告）日：2006-03-09

  The invention provides novel pyrophosphate synthase inhibitors of formula I as well as compositions comprising such inhibitors and methods for their use.

  这项发明提供了一种新型的焦磷酸合酶抑制剂，其化学式为I，以及包含这种抑制剂的组合物和使用它们的方法。
• GERANYLGERANYL PYROPHOSPHATE SYNTHASE INHIBITORS
  申请人：University of Iowa Research

  公开号：EP1793832A2

  公开（公告）日：2007-06-13
• US7268124B2
  申请人：——

  公开号：US7268124B2

  公开（公告）日：2007-09-11
• [EN] GERANYLGERANYL PYROPHOSPHATE SYNTHASE INHIBITORS<br/>[FR] INHIBITEURS DE LA GERANYLGERANYL PYROPHOSPHATE SYNTHASE
  申请人：UNIV IOWA RES FOUND

  公开号：WO2006026380A2

  公开（公告）日：2006-03-09

  The invention provides novel pyrophosphate synthase inhibitors of formula (I), wherein R1 is a saturated or unsaturated: (C5-C20)alkyl chain that optionally comprises one or more aryl rings in the chain and that is optionally substituted with one or more halo, trifluoromethyl, -ORa, -P(=O)(ORa)2, or -NRbRc; R2 is a saturated or unsaturated (C5-C20)alkyl chain that optionally comprises one or more aryl rings in the chain and that is optionally substituted with one or more halo, trifluoromethyl, -ORa, -P(=O)(ORa)2, or -NRbRc; R2; each R3, R4, R5, and R6 is independently OH or (C1-C6)alkoxy; each Ra is independently H, (C1-C6)alkyl, or aryl; and .each Rb and Rc is independently H, (C1-C6)alkyl, or aryl; or Rb and Rc together with the nitrogen to which they are attached form a pyrrolidino, piperidino, morpholino, or thiomorpholino ring; wherein any aryl is optionally substituted with one or more (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkanoyl, (C1-C6)alkanoyloxy, (C1-C6)alkoxycarbonyl, halo, cyano, nitro, carboxy, trifluoromethyl, trifluoromethoxy, NRdRe, or S(O)2NRdRe, wherein each Rd and Re is independently H or (C1-C6)alkyl; or a pharmaceutically acceptable salt or prodrug thereof. Also provided are compositions comprising such inhibitors and methods for their use.
• Synthesis of fluorescently tagged isoprenoid bisphosphonates that inhibit protein geranylgeranylation
  作者：Mona A. Maalouf、Andrew J. Wiemer、Craig H. Kuder、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2007.01.002

  日期：2007.3

  Geminal bisphosphonates call be used for a variety of purposes in human disease including reduction of bone resorption in osteoporosis, treatment of fractures associated with malignancies of the prostate, breast, and lung, and direct anticancer activity against bone marrow derived malignancies. Previous research led to identification of some novel isoprenoid bisphosplionates that inhibit geranylgeranyl pyrophosphate (GGPP) synthesis and diminish protein geranylgeranylation. Described here is the synthesis of fluorescent anthranilate analogues of the most active isoprenoid bisphosphonates and examine their ability to impact post-translational processing of the small GTPases Ras, Rap I a, and Rab6. Similar to their non-fluorescent counterparts, some of these fluorescent isoprenoid bisphosphonates diminish protein geranylgeranylation. Their biological activity and fluorescent character suggest that they may be useful in studies of bisphosphonate localization both ill Cultured cells and in whole organisms. (c) 2007 Elsevier Ltd. All rights reserved.