(4-amino-3,5-dibromophenyl)acetic acid | 191869-08-6

• 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: (4-amino-3,5-dibromophenyl)acetic acid
• 英文别名: 2-(4-amino-3,5-dibromophenyl)acetic acid
• CAS: 191869-08-6
• 化学式: C₈H₇Br₂NO₂
• 分子量: 308.957
• InChiKey: KIYIWMWVYLKCAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.4±40.0 °C(Predicted)
• 密度：
  2.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-amino-3,5-dibromophenyl)acetic acid 、 N-[2-(4-tert-butylbenzyl)-3-pivaloyloxy-propyl]hydroxylamine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以86%的产率得到2-(4-tert-butylbenzyl)-3-[2-(4-amino-3,5-dibromophenyl)acetamido]propyl pivalate
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001
• 作为产物：
  描述：

  对氨基乙酸苯甲酯 在 Oxone 、 sodium bromide 、 水 、 sodium hydroxide 、 溶剂黄146 作用下， 以 水 、 丙酮 、 四氢呋喃 为溶剂， 反应 14.05h， 生成 (4-amino-3,5-dibromophenyl)acetic acid 、 (4-氨基-3-溴苯基)乙酸
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001

文献信息

• UNUSUALLY POTENT ABA RECEPTOR PAN-ANTAGONISTS
  申请人：The Regents of the University of California

  公开号：US20200397000A1

  公开（公告）日：2020-12-24

  The present invention sets forth new compounds that potently block activation of ABA receptors. In some aspects, these compounds can be used to enhance germination of crop seeds to stand establishment and to increase transpiration and photosynthetic yields when water is not limiting plant growth.

  本发明提出了一种新的化合物，可以有效地阻断ABA受体的激活。在某些方面，这些化合物可用于促进作物种子的发芽，以帮助植物生长并增加蒸腾和光合产量，当水分不限制植物生长时。
• US6114390A
  申请人：——

  公开号：US6114390A

  公开（公告）日：2000-09-05