ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate | 413577-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate
• 英文别名: ethyl 2-[2-nitro-4-(phenylmethoxycarbonylamino)naphthalen-1-yl]acetate
• CAS: 413577-71-6
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: HYBXWAMKJBPDCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate 在 platinum(IV) oxide sodium hydroxide 、 硼烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 2-[4-amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate
  参考文献：
  名称：

  Efficient Synthesis of Achiral seco-Cyclopropylbenz[2,3-e]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride

  摘要：

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.

  DOI：

  10.1021/jo060501o
• 作为产物：
  描述：

  氯硝萘 在 sodium sulfide 、 硫酸 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 ethyl [4-(N-benzyloxycarbonylamino)-2-nitronaphthalen-1-yl]acetate
  参考文献：
  名称：

  Efficient Synthesis of Achiral seco-Cyclopropylbenz[2,3-e]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride

  摘要：

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.

  DOI：

  10.1021/jo060501o

文献信息

• Compositions and methods of the use thereof achiral analogues of CC-1065 and the duocarmycins
  申请人：Taiho Pharmaceutical Co. Ltd.

  公开号：US06660742B2

  公开（公告）日：2003-12-09

  The present invention relates to novel achiral seco-analogues of DNA minor groove and sequence-selective alkylating agents (+)-CC1065 and the duocarmycins, depicted as general class I, II, III, IV and V: wherein X is a good leaving group, such as a chloride, a bromide, an iodide, a mesylate, a tosylate, an acetate, a quaternary ammonium moiety, a mercaptan, an alkylsulfoxyl, or an alkylsulfonyl group, preferably either a chloride, a bromide, or an iodide group. R1 is a suitable minor groove binding agent to enhance the interactions of the achiral seco-cyclopropaneindole (Cl) or an achiral seco-duocarmycin with specific sequences of DNA.

  该发明涉及一种新颖的DNA次级沟和序列选择性烷基化剂（+）-CC1065和duocarmycins的不对称环丙烷各向同性衍生物，表示为一般的I、II、III、IV和V类：其中X是一个良好的离去基团，如氯化物、溴化物、碘化物、甲磺酸酯、对甲苯磺酸酯、乙酸酯、季铵基团、巯基、烷基亚砜基或烷基磺酰基，最好是氯化物、溴化物或碘化物基团。R1是一个适当的次级沟结合剂，用于增强不对称环丙烷吲哚（Cl）或不对称duocarmycin与DNA特定序列的相互作用。
• Efficient Synthesis of Achiral <i>s</i><i>eco</i>-Cyclopropylbenz[2,3-<i>e</i>]indoline Analogues:  [4-Amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride and [4-Hydroxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl Chloride
  作者：Atsushi Sato、Adrienne Scott、Tetsuji Asao、Moses Lee

  DOI：10.1021/jo060501o

  日期：2006.6.1

  Achiral seco-aminocyclopropylbenz[ 2,3-e] indoline and secohydroxycyclopropylbenz[ 2,3-e] indoline ( seco-CBI) analogues of the duocarmycins and CC-1065, e. g., 7 and 8, are potent anticancer agents. This paper describes significantly improved synthetic strategies for preparing these compounds. Starting from Martius acid ( 9), the new strategy gave a 13-fold increase in the overall yield of 7, and the use of ditertbutyl malonate was economically beneficial. For compound 8, the new strategy employed an Emmons-Horner reaction, followed by a Stobbe condensation, and the overall yield was improved 15-fold.