(4-acetoxy-2-iodo-5-methoxyphenyl)acetic acid | 412271-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (4-acetoxy-2-iodo-5-methoxyphenyl)acetic acid
• 英文别名: 4-acetoxy-2-iodo-5-methoxyphenylacetic acid；2-Iodo-4-acetoxy-5-methoxyphenylacetic acid；2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetic acid
• CAS: 412271-92-2
• 化学式: C₁₁H₁₁IO₅
• 分子量: 350.11
• InChiKey: KSGWASICJLYWCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-acetoxy-2-iodo-5-methoxyphenyl)acetic acid 在 四氢吡咯 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-2-iodo-5-methoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

  摘要：

  Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00127-0
• 作为产物：
  描述：

  高香草酸 在 硫酸 、 碘 、 silver trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4-acetoxy-2-iodo-5-methoxyphenyl)acetic acid
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

  摘要：

  Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00127-0

文献信息

• Novel labeled resiniferatoxin derivatives
  申请人：——

  公开号：US20040230064A1

  公开（公告）日：2004-11-18

  This invention relates to resiniferatoxin derivatives useful in a vanilloid receptor binding assay and methods for production thereof.

  本发明涉及树脂花生四烯酸酯衍生物，其在vanilloid受体结合测定中有用，并提供其制备方法。
• Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin
  作者：Dong Wook Kang、Yong Soo Kim、Kwang Su Lim、Myeong Seop Kim、Larry V. Pearce、Vladimir A. Pavlyukovets、Andy K. Tao、Krystle A. Lang-Kuhs、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmc.2010.09.001

  日期：2010.11.15

  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.
• NOVEL LABELED RESINIFERATOXIN DERIVATIVES
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP1341795A2

  公开（公告）日：2003-09-10
• US7112685B2
  申请人：——

  公开号：US7112685B2

  公开（公告）日：2006-09-26
• [EN] NOVEL LABELED RESINIFERATOXIN DERIVATIVES<br/>[FR] DERIVES DE RESINIFERATOXINE NOUVELLEMENT MARQUES
  申请人：ORTHO MCNEIL PHARM INC

  公开号：WO2002030937A2

  公开（公告）日：2002-04-18

  This invention relates to resiniferatoxin derivatives useful in a vanilloid receptor binding assay and methods for production thereof.