N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide | 478249-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide
• 英文别名: N-[(4-methoxyphenyl)methyl]-1H-pyrrole-2-carboxamide
• CAS: 478249-53-5
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: DOJIPVBZQZECLY-UHFFFAOYSA-N

物化性质

• 沸点：
  514.5±35.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)
• 溶解度：
  >34.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 4-甲氧基苄胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以20%的产率得到N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin

  摘要：

  Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl) allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI(50)) of 42 mu M in MCF-7 (breast) cells and 24 mu M in A2780 (ovarian) cells and >50 mu M in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI(50) values of <5 mu M were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.021

文献信息

• ORGANIC METAL COMPLEXES FOR USE IN OPTOELECTRONIC DEVICES
  申请人：Chichak Kelly Scott

  公开号：US20100156278A1

  公开（公告）日：2010-06-24

  The invention provides an organic metal complex represented by the formula (I), wherein M is a metal selected from Rh, Ir, or Pt; Y represents N or O; R 1 represents a hydrogen, a halogen, a nitro group, an amino group, a hydroxyl group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, and a C 3 -C 50 cycloaliphatic radical; R 2 represents a hydrogen, C 3 -C 20 aromatic radical, C 1 -C 50 aliphatic radical, or a C 3 -C 50 cycloaliphatic radical; or R 1 and R 2 , together with the adjacent Y, may form a ring, preferably a 5- or 6-membered ring; n 1 has a value of from 0 to 3; and n 2 has a value of 0 to 2; m 1 has a value of at least 1; and m 2 has a value of at least 1 provided that m 1 +m 2 is 3.

  本发明提供了一种有机金属配合物，其化学式表示为（I），其中M是从Rh，Ir或Pt中选择的金属; Y代表N或O; R1表示氢，卤素，硝基，氨基，羟基，C3-C40芳基，C1-C50脂肪基和C3-C50环脂肪基中的一种; R2表示氢，C3-C20芳基，C1-C50脂肪基或C3-C50环脂肪基中的一种; 或R1和R2与相邻的Y一起形成一个环，优选为5-或6-成员环; n1的值为0至3; n2的值为0至2; m1的值至少为1; m2的值至少为1，前提是m1+m2为3。
• [EN] ORGANIC METAL COMPLEXES FOR USE IN OPTOELECTRONIC DEVICES<br/>[FR] COMPLEXES DE MÉTAUX ORGANIQUES DESTINÉS À ÊTRE UTILISÉS DANS DES DISPOSITIFS OPTOÉLECTRONIQUES
  申请人：GEN ELECTRIC

  公开号：WO2010074957A1

  公开（公告）日：2010-07-01

  The invention provides an organic metal complex represented by the formula (I), wherein M is a metal selected from Rh, Ir, or Pt; Y represents N or O; R1 represents a hydrogen, a halogen, a nitro group, an amino group, a hydroxyl group, a C3-C40 aromatic radical, a C1-C50 aliphatic radical, and a C3-C50 cycloaliphatic radical; R2 represents a hydrogen, C3- C20 aromatic radical, C1-C50 aliphatic radical, or a C3-C50 cycloaliphatic radical; or R1 and R2, together with the adjacent Y, may form a ring, preferably a 5- or 6-membered ring; n1 has a value of from O to 3; and n2 has a value of O to 2; mi has a value of at least 1; and m2 has a value of at least 1 provided that m1+m2 is 3.
• Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin
  作者：Lauren Dyson、Anthony D. Wright、Kelly A. Young、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.bmc.2014.01.021

  日期：2014.3

  Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl) allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI(50)) of 42 mu M in MCF-7 (breast) cells and 24 mu M in A2780 (ovarian) cells and >50 mu M in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI(50) values of <5 mu M were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. (C) 2014 Elsevier Ltd. All rights reserved.