tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate | 1224567-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate
• 英文别名: 3-(3-tert-butoxycarbonylaminopropoxy)-N-(4-chlorophenyl)-2-naphthamide；3-(3-tert-Butoxylcarbonylaminopropoxy)-N-(4-chlorophenyl)-2-naphthamide；tert-butyl N-[3-[3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl]oxypropyl]carbamate
• CAS: 1224567-51-4
• 化学式: C₂₅H₂₇ClN₂O₄
• 分子量: 454.953
• InChiKey: QGTKUMBRLPWFGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate 在 盐酸 作用下， 以 甲醇 、 乙醚 、 氯仿 为溶剂， 以100%的产率得到3-(3-aminopropoxy)-N-(4-chlorophenyl)-2-naphthamide
  参考文献：
  名称：

  Identification of a Potent Inhibitor of CREB-Mediated Gene Transcription with Efficacious in Vivo Anticancer Activity

  摘要：

  Recent studies have shown that nuclear transcription factor cyclic adenosine monophosphate response element binding protein (CREB) is overexpressed in many different types of cancers. Therefore, CREB has been pursued as a novel cancer therapeutic target. Naphthol AS-E and its closely related derivatives have been shown to inhibit CREB-mediated gene transcription and cancer cell growth. Previously, we identified naphthamide 3a as a different chemotype to inhibit CREB's transcription activity. In a continuing effort to discover more potent CREB inhibitors, a series of structural congeners of 3a was designed and synthesized. Biological evaluations of these compounds uncovered compound 3i (666-15) as a potent and selective inhibitor of CREB-mediated gene transcription (IC50 = 0.081 +/- 0.04 mu M). 666-15 also potently inhibited cancer cell growth without harming normal cells. In an in vivo MDA-MB-468 xenograft model, 666-15 completely suppressed the tumor growth without overt toxicity. These results further support the potential of CREB as a valuable cancer drug target.

  DOI：

  10.1021/acs.jmedchem.5b00468
• 作为产物：
  描述：

  N-(3-羟丙基)氨基甲酸叔丁酯 、 色酚 AS-E 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到tert-butyl (3-((3-((4-Chlorophenyl)carbamoyl)naphthalen-2-yl)oxy)propyl)carbamate
  参考文献：
  名称：

  [EN] NAPHTHAMIDES AS ANTICANCER AGENTS
  [FR] NAPHTHAMIDES EN TANT QU'AGENTS ANTI-CANCÉREUX

  摘要：

  一种化合物（特别适用于抑制癌症），其化学式为（I）或其药学上可接受的盐，其中：x为0或1；R1-R6各自独立地为H，-CN，-NO2，-NO，-OH，卤素，羟基烷基，羧基，取代羧基，氨基甲酰基，烷氧基，羰基或取代羰基；R7为H，烷基，烷基氨基，氨基酰基，羟基酰基，杂环芳基，杂环环烷基，烷基杂环芳基或烷基杂环环烷基；R8为H或烷基；A为O或N；Ar为芳基，取代芳基，杂环芳基或取代杂环芳基，但如果R7为H，则Ar为取代烷基氨基的芳基。

  公开号：

  WO2010048302A1

文献信息

• NAPHTHAMIDES AS ANTICANCER AGENTS
  申请人：Xiao Xiangshu

  公开号：US20110301179A1

  公开（公告）日：2011-12-08

  A compound (particularly useful for inhibiting cancer) according to formula I: or a pharmaceutically acceptable salt thereof, wherein: x is 0 or 1; R 1 -R 6 are each independently H, —CN, —NO 2 , —NO, —OH, halogen, hydroxyalkyl, carboxyl, substituted carboxyl, aminocarbonyl, alkoxy, carbonyl or substituted carbonyl; R 7 is H, alkyl, alkyl amino, aminoacyl, hydroxyacyl, heteroaryl, heterocycloalkyl, alkyl heteroaryl or alkyl heterocycloalkyl; R 8 is H or alkyl; A is O or N; and Ar is an aryl, substituted aryl, heteroaryl, or substituted heteroaryl, provided that if R 7 is H then Ar is aryl substituted with alkyl amino.

  一种化合物（在抑制癌症方面特别有用），其化学式为I：或其药学上可接受的盐，其中：x为0或1; R1-R6分别独立地为H，—CN，—NO2，—NO，—OH，卤素，羟基烷基，羧基，取代羧基，氨基甲酰基，烷氧基，羰基或取代羰基; R7为H，烷基，烷基氨基，氨基酰基，羟基酰基，杂环芳基，杂环烷基，烷基杂环芳基或烷基杂环烷基; R8为H或烷基; A为O或N; Ar为芳基，取代芳基，杂环芳基或取代杂环芳基，但如果R7为H，则Ar为取代了烷基氨基的芳基。
• Naphthamides as anticancer agents
  申请人：Xiao Xiangshu

  公开号：US08653086B2

  公开（公告）日：2014-02-18

  A compound (particularly useful for inhibiting cancer) according to formula I: or a pharmaceutically acceptable salt thereof, wherein: x is 0 or 1; R1-R6 are each independently H, —CN, —NO2, —NO, —OH, halogen, hydroxyalkyl, carboxyl, substituted carboxyl, aminocarbonyl, alkoxy, carbonyl or substituted carbonyl; R7 is H, alkyl, alkyl amino, aminoacyl, hydroxyacyl, heteroaryl, heterocycloalkyl, alkyl heteroaryl or alkyl heterocycloalkyl; R8 is H or alkyl; A is O or N; and Ar is an aryl, substituted aryl, heteroaryl, or substituted heteroaryl, provided that if R7 is H then Ar is aryl substituted with alkyl amino.

  一种化合物（特别是用于抑制癌症）的化学式为I：或其药学上可接受的盐，其中：x为0或1；R1-R6各自独立地为H，-CN，-NO2，-NO，-OH，卤素，羟基烷基，羧基，取代羧基，氨基甲酰基，烷氧基，羰基或取代羰基；R7为H，烷基，烷基氨基，氨基酰基，羟基酰基，杂环芳基，杂环环烷基，烷基杂环芳基或烷基杂环环烷基；R8为H或烷基；A为O或N；Ar为芳基，取代芳基，杂芳基或取代杂芳基，但如果R7为H，则Ar为烷基氨基取代的芳基。
• US8653086B2
  申请人：——

  公开号：US8653086B2

  公开（公告）日：2014-02-18