N-Cbz-4-amino-2,6-dichlorophenol | 1021693-53-7

• 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: N-Cbz-4-amino-2,6-dichlorophenol
• 英文别名: benzyl N-(3,5-dichloro-4-hydroxyphenyl)carbamate
• CAS: 1021693-53-7
• 化学式: C₁₄H₁₁Cl₂NO₃
• 分子量: 312.152
• InChiKey: HTUPVJMFLHZEOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Cbz-4-amino-2,6-dichlorophenol 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成 N-(3,5-dichloro-4-(2-(Boc-amino)ethoxy)phenyl)formamide
  参考文献：
  名称：

  Discovery and SAR of Novel and Selective Inhibitors of Urokinase Plasminogen Activator (uPA) with an Imidazo[1,2-a]pyridine Scaffold

  摘要：

  Urokinase plasminogen activator (uPA) is a biomarker and therapeutic target for several cancer types. Its inhibition is regarded as a promising, noncytotoxic approach in cancer therapy by blocking growth and/or metastasis of solid tumors. Earlier, we reported the modified substrate activity screening (MSAS) approach and applied it for the identification of fragments with affinity for uPA's Si pocket. Here, these fragments are transformed into a novel class of uPA inhibitors with an imidazo[1,2-a]pyridine scaffold. The SAR for uPA inhibition around this scaffold is explored, and the best compounds in the series have nanomolar uPA affinity and selectivity with respect to the related trypsin-like serine proteases (thrombin, tPA, FXa, plasmin, plasma kallikrein, trypsin, FVIIa). Finally, the approach followed for translating fragments into small molecules with a decorated scaffold architecture is conceptually straightforward and can be expected to be broadly applicable in fragment-based drug design.

  DOI：

  10.1021/acs.jmedchem.5b01171
• 作为产物：
  描述：

  2,6-二氯-4-氨基苯酚 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到N-Cbz-4-amino-2,6-dichlorophenol
  参考文献：
  名称：

  Discovery and SAR of Novel and Selective Inhibitors of Urokinase Plasminogen Activator (uPA) with an Imidazo[1,2-a]pyridine Scaffold

  摘要：

  Urokinase plasminogen activator (uPA) is a biomarker and therapeutic target for several cancer types. Its inhibition is regarded as a promising, noncytotoxic approach in cancer therapy by blocking growth and/or metastasis of solid tumors. Earlier, we reported the modified substrate activity screening (MSAS) approach and applied it for the identification of fragments with affinity for uPA's Si pocket. Here, these fragments are transformed into a novel class of uPA inhibitors with an imidazo[1,2-a]pyridine scaffold. The SAR for uPA inhibition around this scaffold is explored, and the best compounds in the series have nanomolar uPA affinity and selectivity with respect to the related trypsin-like serine proteases (thrombin, tPA, FXa, plasmin, plasma kallikrein, trypsin, FVIIa). Finally, the approach followed for translating fragments into small molecules with a decorated scaffold architecture is conceptually straightforward and can be expected to be broadly applicable in fragment-based drug design.

  DOI：

  10.1021/acs.jmedchem.5b01171

文献信息

• Aminophenoxyacetamide derivatives and pharmaceutical composition containing thereof
  申请人：——

  公开号：US20030139447A1

  公开（公告）日：2003-07-24

  There is provided an aminophenoxyacetamide derivative of the formula (I): wherein, R 1 to R 4 are, independent from each other, hydrogen atom; optionally substituted alkyl group; E 1 is —NR 4 — and E 2 is oxygen atom or —NR 10 ; Q is group —X—Y—Q′ (X and Y are connecting bond; X is alkylene or alkenylene group, etc.; Y is selected from the groups consisting of C═O, NHC(═O), C(═O)NH, etc.; Q′ is hydrogen atom or pheny, pyridyl groups which may be substituted, etc.), or a pharmaceutically acceptable salt thereof. These compounds have neuroprotective effect by introducing the CalbindinD-28k, one of Ca 2+ -binding proteins. 11

  提供了一种氨基苯氧乙酰胺衍生物，其化学式为(I)：其中，R1至R4独立地为氢原子；可选择取代的烷基基团；E1为—NR4—，E2为氧原子或—NR10；Q为基团—X—Y—Q′（X和Y为连接键；X为烷基或烯基基团等；Y选自由C═O、NHC(═O)、C(═O)NH等组成的基团；Q′为氢原子或苯基、可取代的吡啶基团等），或其药学上可接受的盐。这些化合物通过引入钙结合蛋白之一的CalbindinD-28k具有神经保护作用。
• Arylipiperdinopropanol and arylipiperazinopropanol derivatives and pharmaceuticals containing the same
  申请人：Annoura Hirokazu

  公开号：US20050101610A1

  公开（公告）日：2005-05-12

  A compound having the formula (I) or its salt, hydrate, hydrate salt or solvate: wherein R 1 to R 4 independently represent H, halogen, OH, alkoxy, optionally substituted alkyl, aryl, or aralkyl group, R 5 represents H, optionally substituted alkyl, aryl, or aralkyl group, E 1 represents O, S, or —NR 6 , where R 6 represents H, an optionally substituted alkyl, aryl, or aralkyl group, E 2 represents O, S, or —NR 7 , where R 7 represents H, an optionally substituted alkyl, aryl, or aralkyl group, A represents CH, C(OH), or N, X represents H, halogen, alkoxy, or an optionally substituted alkyl group, and Q represents an optionally substituted phenyl group, phenoxy, phenylmethyl, or cycloalkyloxy group, where when E 1 represents O or S, E 2 does not represent O or S, which has an action of suppressing the cytotoxic Ca 2+ overload and lipid peroxidation and effective for pharmaceutical preparation for the alleviation and treatment of symptoms due to ischemic diseases, etc.

  化合物具有以下公式(I)或其盐，水合物，水合盐或溶剂化物： 其中，R1至R4独立地表示H，卤素，OH，烷氧基，可选择取代的烷基，芳基或芳基烷基，R5表示H，可选择取代的烷基，芳基或芳基烷基，E1表示O，S或-NR6，其中R6表示H，可选择取代的烷基，芳基或芳基烷基，E2表示O，S或-NR7，其中R7表示H，可选择取代的烷基，芳基或芳基烷基，A表示CH，C（OH）或N，X表示H，卤素，烷氧基或可选择取代的烷基，Q表示可选择取代的苯基，苯氧基，苯甲基或环烷氧基，其中当E1表示O或S时，E2不表示O或S，该化合物具有抑制细胞毒性Ca2+过载和脂质过氧化作用，并且对于缓解和治疗缺血性疾病症状等方面的制药制剂具有有效作用。
• Aminophenoxyacetic acid derivatives and pharmaceutical composition containing thereof
  申请人：Annoura Hirokazu

  公开号：US20050245574A1

  公开（公告）日：2005-11-03

  There is provided an aminophenoxyacetic acid derivative of the following formula (I): wherein, R 1 , R 2 , R 3 and R 4 are, independent from each other, alkoxy group, alkyl group or aryl group, etc.; E 1 and E 2 are oxygen atom, sulfur atom, etc.; n is 0 to 5; X and Y are alkylene group, cycloalkylen group, or alkenylen group; Q is pheny group which may be substituted or benzoyl group, etc, or a pharmaceutically acceptable salt thereof. These compounds have neuroprotective effects by inducing calbindin D28Kd, one of Ca 2+ -binding proteins.

  提供了以下式子（I）的氨基苯氧乙酸衍生物： 其中，R1、R2、R3和R4是独立的烷氧基、烷基或芳基等基团；E1和E2是氧原子、硫原子等；n为0到5；X和Y是烷基、环烷基或烯基等；Q是苯基，可能被取代或苯甲酰基等，或其药学上可接受的盐。 这些化合物通过诱导钙结合蛋白之一的钙结合蛋白D28Kd具有神经保护作用。
• Arylpiperidinopropanol and arylpiperazinopropanol derivatives and pharmaceuticals containing the same
  申请人：——

  公开号：US20030236269A1

  公开（公告）日：2003-12-25

  A compound having the formula (I) or its salt, hydrate, hydrate salt or solvate: 1 wherein R 1 to R 4 independently represent H, halogen, OH, alkoxy, optionally substituted alkyl, aryl, or aralkyl group, R 5 represents H, optionally substituted alkyl, aryl, or aralkyl group, E 1 represents O, S, or —NR 6 , where R 6 represents H, an optionally substituted alkyl, aryl, or aralkyl group, E 2 represents O, S, or —NR 7 , where R 7 represents H, an optionally substituted alkyl, aryl, or aralkyl group, A represents CH, C(OH), or N, X represents H, halogen, alkoxy, or an optionally substituted alkyl group, and Q represents an optionally substituted phenyl group, phenoxy, phenylmethyl, or cycloalkyloxy group, where when E 1 represents O or S, E 2 does not represent O or S, which has an action of suppressing the cytotoxic Ca 2+ overload and lipid peroxidation and effective for pharmaceutical preparation for the alleviation and treatment of symptoms due to ischemic diseases, etc.

  化合物具有公式(I)或其盐、水合物、水合盐或溶剂化物：其中R1至R4独立地表示H、卤素、OH、烷氧基、可选地取代的烷基、芳基或芳基烷基，R5表示H、可选地取代的烷基、芳基或芳基烷基，E1表示O、S或-NR6，其中R6表示H、可选地取代的烷基、芳基或芳基烷基，E2表示O、S或-NR7，其中R7表示H、可选地取代的烷基、芳基或芳基烷基，A表示CH、C（OH）或N，X表示H、卤素、烷氧基或可选地取代的烷基基团，Q表示可选地取代的苯基、苯氧基、苯甲基或环烷氧基基团，当E1表示O或S时，E2不表示O或S，该化合物具有抑制细胞毒性Ca2+过载和脂质过氧化作用，对于缓解和治疗缺血性疾病症状等方面的制药制剂具有有效作用。
• PURINES AS PKC-THETA INHIBITORS
  申请人：Neagu Irina

  公开号：US20110046131A1

  公开（公告）日：2011-02-24

  A chemical genus of purines, which are useful as PKCθ inhibitors, is disclosed. The genus is represented by the formula (I); A representative example is: (II)

  揭示了一种嘌呤的化学属，其作为PKCθ抑制剂具有用处。该属由公式（I）表示；代表性例子为：（II）。