(E)-3-(ethoxycarbonyl)-4-(4-nitrophenyl)-3-butenic acid | 222535-04-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(ethoxycarbonyl)-4-(4-nitrophenyl)-3-butenic acid
• 英文别名: (E)-3-ethoxycarbonyl-4-(4-nitrophenyl)but-3-enoic acid
• CAS: 222535-04-8
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: XZTMCQVLKCDOCK-JXMROGBWSA-N

物化性质

• 沸点：
  444.6±40.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (E)-3-(ethoxycarbonyl)-4-(4-nitrophenyl)-3-butenic acid 在 sodium acetate 作用下， 反应 12.0h， 生成 4-(乙酰基氧基)-6-硝基-2-萘羧酸乙酯
  参考文献：
  名称：

  Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 H -benz[ e ]indole ( seco -CBI) dimers

  摘要：

  Three types of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) dimers were designed, synthesized and evaluated in vitro by NCI against nine types of cancer cells. Biological results showed that the antitumor activities of these seco-CBI dimers were strongly related to the position and length of the linker and generally with potency increasing in the order of C7-C7 dimers (22i-iv) < C7-N3 dimers (28i-iv) < N3-N3 dimers (25i-iv). Compound 28iv showed significant activity against CCRT-CEM, HL-60 (TB), MOLT-4, and SR leukemia cell lines and the MCF 7 breast cancer cell line with GI(50) values < 0.01 mu M. N3-N3 dimer 25i displayed striking potency against leukemia, CNS cancer, melanoma and prostate cancer cell lines with GI(50) values < 0.01 mu M against all the cell lines and showed the highest overall potency of the agents examined (GMG = 0.0120 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00088-2
• 作为产物：
  描述：

  1-乙基4-(叔-丁基)2-(二乙基膦酰)琥珀酸盐 在 水 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 (E)-3-(ethoxycarbonyl)-4-(4-nitrophenyl)-3-butenic acid
  参考文献：
  名称：

  Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 H -benz[ e ]indole ( seco -CBI) dimers

  摘要：

  Three types of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) dimers were designed, synthesized and evaluated in vitro by NCI against nine types of cancer cells. Biological results showed that the antitumor activities of these seco-CBI dimers were strongly related to the position and length of the linker and generally with potency increasing in the order of C7-C7 dimers (22i-iv) < C7-N3 dimers (28i-iv) < N3-N3 dimers (25i-iv). Compound 28iv showed significant activity against CCRT-CEM, HL-60 (TB), MOLT-4, and SR leukemia cell lines and the MCF 7 breast cancer cell line with GI(50) values < 0.01 mu M. N3-N3 dimer 25i displayed striking potency against leukemia, CNS cancer, melanoma and prostate cancer cell lines with GI(50) values < 0.01 mu M against all the cell lines and showed the highest overall potency of the agents examined (GMG = 0.0120 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00088-2

文献信息

• [EN] ASYMMETRIC CONJUGATE COMPOUNDS<br/>[FR] COMPOSÉS CONJUGUÉS ASYMÉTRIQUES
  申请人：FEMTOGENIX LTD

  公开号：WO2017194960A1

  公开（公告）日：2017-11-16

  The invention relates to compound of formula (I): A-X1-L-X2-B and salts, solvates and tautomers thereof, which are useful as medicaments, in particular as anti-proliferative agents and for use as a drug in an antibody-drug conjugate; wherein A is a group selected from (A1), (A2), (A3), (A4) and (A5); X1 and X2 are independently selected from O, S, NR28, CR28R29, CR28R29O, C(=O), C(=O)NR28, NR28C(=O), C(O)-RA-C(O)-NH, C(O)-RA-NH-C(O), C(O) -NH-RA-C(O), NH-C(O)-RA-C(O), NH-C(O)-RA-C(O)-NH, NH-C(O)-RA-NH-C(O), C(O)-NH-RA-NH-C(O), C(O)-NH-RA-C(O)-NH, O-C(O) and C(O)-O or is absent; L is selected from an amino acid, a peptide chain having from 2 to 12 amino acids, a paraformaldehyde chain –(OCH2)1-24-, a polyethylene glycol chain -(OCH2CH2)1-12- and –(CH2)m-Y6-(CH2)n- wherein Y6 is selected from –(CH2)z- and a group (L1) a group (L1) that is selected from arylene, monocyclic heteroarylene, monocyclic cycloalkylene, monocyclic cycloalkenylene and monocyclic heterocyclylene groups optionally substituted with up to three optional substituent groups; and B is a polycyclic group selected from (B1), (B2) and (B3).

  该发明涉及化合物的公式(I)：A-X1-L-X2-B及其盐、溶剂合物和互变异构体，其作为药物具有实用性，特别是作为抗增殖剂并用作抗体药物结合物中的药物；其中A是从(A1)、(A2)、(A3)、(A4)和(A5)中选择的基团；X1和X2分别选择自O、S、NR28、CR28R29、CR28R29O、C(=O)、C(=O)NR28、NR28C(=O)、C(O)-RA-C(O)-NH、C(O)-RA-NH-C(O)、C(O)-NH-RA-C(O)、NH-C(O)-RA-C(O)、NH-C(O)-RA-C(O)-NH、NH-C(O)-RA-NH-C(O)、C(O)-NH-RA-NH-C(O)、C(O)-NH-RA-C(O)-NH、O-C(O)和C(O)-O或者不存在；L选择自氨基酸、具有2至12个氨基酸的肽链、对甲醛链-(O )1-24-、聚乙二醇链-(O )1-12-和-(CH2)m-Y6-( )n-，其中Y6选择自-( )z-和一个基团(L1)，该基团(L1)选择自芳基、单环杂芳基、单环环烷基、单环环烯烃基和单环杂环烷基，可选地取代高达三个可选取代基团；B是从(B1)、(B2)和(B3)中选择的多环基团。
• AN EFFICIENT METHOD FOR THE SYNTHESIS OF SUBSTITUTED 4-ACETOXYNAPHTHALENE-2-CARBOXYLATE ESTERS, ETHYL 4-ACETOXYBENZOFURAN-6-CARBOXYLATE, AND ETHYL 4-ACETOXYBENZOTHIOPHENE-6-CARBOXYLATE
  作者：Hari Pati、Regan LeBlanc、Moses Lee

  DOI：10.1515/hc.2003.9.6.587

  日期：2003.1