5-Iod-vanillin | 89942-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-Iod-vanillin
• 英文别名: 2-iodo-4-hydroxy-3-methoxybenzaldehyde；4-hydroxy-2-iodo-3-methoxy-benzaldehyde；4-Hydroxy-2-jod-3-methoxy-benzaldehyd；2-iodo-vanillin；iodovanillin；4-Hydroxy-2-iodo-3-methoxybenzaldehyde
• CAS: 89942-36-9
• 化学式: C₈H₇IO₃
• 分子量: 278.046
• InChiKey: GARSAGRBWBKYSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Iod-vanillin 在 sodium tetrahydroborate 、 二苯基磷酸 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 0.5h， 生成 2-Iodo-3-methoxy-4-(2-methoxy-ethoxymethoxy)-benzylamine
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 5-Iod-vanillin
  参考文献：
  名称：

  Iodine Substitution Products of Vanillin and Some of their Derivatives

  摘要：

  DOI：

  10.1021/ja01315a054

文献信息

• Intermediates to tetrahydro-beta-carbolines
  申请人：Eli Lilly and Company

  公开号：US05635528A1

  公开（公告）日：1997-06-03

  3-Ethanamine and 3-ethanamine related compounds are provided that are useful intermediates and have beneficial central nervous system activity.

  3-乙胺和3-乙胺相关化合物被提供，它们是有用的中间体，并且具有有益的中枢神经系统活性。
• Method for treating 5HT.sub.2B receptor related conditions
  申请人：Eli Lilly and Company

  公开号：US05688807A1

  公开（公告）日：1997-11-18

  The present invention provides methods for binding a 5-HT.sub.2B receptor in mammals using a both known and novel compounds. Further, the invention provides a method for treating or preventing 5-HT.sub.2B related conditions. Finally, the invention provides an article of manufacture.

  本发明提供了一种方法，用于结合哺乳动物中的5-HT.sub.2B受体，使用已知和新型化合物。此外，本发明提供了一种治疗或预防5-HT.sub.2B相关疾病的方法。最后，本发明提供了一种制造品。
• First Total Syntheses of (.+-.)-Isopiline, (.+-.)-Preocoteine, (.+-.)-Oureguattidine and (.+-.)-3-Methoxynordomesticine and the Biological Activities of (.+-.)-3-Methoxynordomesticine
  作者：Surachai Nimgirawath、Phansuang Udomputtimekakul、Thongchai Taechowisan、Asawin Wanbanjob、Yuemao Shen

  DOI：10.1248/cpb.57.368

  日期：——

  convenient and economical synthesis of 4-hydroxy-2,3-dimethoxybenzaldehyde has been developed. This was used as the starting material for the first total syntheses of (+/-)-isopiline, (+/-)-preocoteine, (+/-)-oureguattidine and (+/-)-3-methoxynordomesticine in which the key step involved formation of ring C of the aporphines by a radical-initiated cyclisation. Although (+/-)-3-methoxynordomesticine

  已经开发了方便且经济的4-羟基-2，3-二甲氧基苯甲醛的合成。将其用作（+/-）-异脯氨酸，（+/-）-preocoteine，（+/-）-尿瓜定和（+/-）-3-甲氧基正十二烷的第一批总合成的原料，其中关键该步骤涉及通过自由基引发的环化作用形成的Aphiphines的C环。虽然（+/-）-3-甲氧基降血压药具有弱的抗菌活性，但它抑制一氧化氮（NO），前列腺素（PG）E（2），肿瘤坏死因子（TNF）-α，白介素（IL）-1的产生β和IL-6以及LPS刺激的巨噬细胞中诱导型一氧化氮合酶（iNOS）和环氧合酶（COX）-2的表达。
• Tetrahydro-.beta.-carbolines
  申请人：Eli Lilly and Company

  公开号：US05500431A1

  公开（公告）日：1996-03-19

  The present invention provides tetrahydro-betacarboline compounds having useful central nervous system activity.

  本发明提供了具有有用的中枢神经系统活性的四氢-β-咔啉化合物。
• Tetrahydro-beta-carbolines
  申请人：Eli Lilly and Company

  公开号：US05760051A1

  公开（公告）日：1998-06-02

  Tetrahydro-beta-carboline compounds having useful central nervous system activity are enclosed.

  含有有用的中枢神经系统活性的四氢-β-咔啉化合物已封装。