4-(4-iodo-phenyl)-4H-[1,2,4]triazole | 179421-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-iodo-phenyl)-4H-[1,2,4]triazole
• 英文别名: 1-(4-iodobenzene)-1H-1,3,4-triazole；4-(4-Iodophenyl)-4H-1,2,4-triazole；4-(4-iodophenyl)-1,2,4-triazole
• CAS: 179421-16-0
• 化学式: C₈H₆IN₃
• mdl: MFCD09416977
• 分子量: 271.06
• InChiKey: RGXDSHJOEIOEBM-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-iodo-phenyl)-4H-[1,2,4]triazole 在 Rh(acac)2(CO)2 copper(l) iodide 、 1,10-菲罗啉 、 氢气 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 70.0~80.0 ℃ 、2.0 MPa 条件下， 反应 142.0h， 生成 L-775606
  参考文献：
  名称：

  Synthesis of Pharmacologically Relevant Indoles with Amine Side Chains via Tandem Hydroformylation/Fischer Indole Synthesis

  摘要：

  The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

  DOI：

  10.1021/jo050464l
• 作为产物：
  描述：

  N,N-dimethylformamideazine dihydrochloride 、 对碘苯胺 以 甲苯 为溶剂， 反应 3.5h， 以39%的产率得到4-(4-iodo-phenyl)-4H-[1,2,4]triazole
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041

文献信息

• AROMATIC AMINE AR AND BET TARGETING PROTEIN DEGRADATION CHIMERA COMPOUND AND USE
  申请人：Hinova Pharmaceuticals Inc.

  公开号：EP3971176A1

  公开（公告）日：2022-03-23

  An aromatic amine androgen receptor (AR) and BET targeting protein degradation chimera compound and its use. Specifically provided is a compound represented by formula I. Experimental results show that the compound can target and degrade both AR and BRD4, and down-regulate the expression of AR and BRD4 proteins; the compound can inhibit the proliferation of a variety of prostate cancer cells; the compound can inhibit the proliferation of a prostate cancer cell line LNCaP/AR, which overexpresses the AR, and can achieve a good inhibition effect on a prostate cancer cell line 22RV1, which is resistant to a marketed prostate cancer drug (enzalutamide); the compound also shows good metabolic stability, and has a good application prospect in the preparation of an AR and/or BET protein degradation targeting chimera, and a drug for the treatment of related diseases regulated by the AR and BET.

  一种芳香胺雄激素受体（AR）和BET靶向蛋白降解嵌合物化合物及其用途。具体提供的是由式I表示的化合物。实验结果表明，该化合物可以靶向降解AR和BRD4，并下调AR和BRD4蛋白的表达；该化合物可以抑制多种前列腺癌细胞的增殖；该化合物可以抑制过表达AR的前列腺癌细胞系LNCaP/AR的增殖，并且对一种对市售前列腺癌药物（恩扎鲁胺）具有耐药性的前列腺癌细胞系22RV1具有良好的抑制效果；该化合物还表现出良好的代谢稳定性，在制备AR和/或BET蛋白降解靶向嵌合物和治疗由AR和BET调控的相关疾病的药物方面具有良好的应用前景。
• Synthesis and properties of azole-substituted ferrocenes
  作者：Tomoyuki Mochida、Hirotaka Shimizu、Shinya Suzuki、Takahiro Akasaka

  DOI：10.1016/j.jorganchem.2006.08.020

  日期：2006.11

  4-Ferrocenyltriazole, 4-(4-ferrocenylphenyl)triazole, 4-ferrocenyltetrazole, and 4-(4-ferrocenylphenyl)tetrazole have been prepared. Redox potentials and decomposition temperatures were evaluated and all the compounds were crystallographically characterized; in most cases, weak intermolecular (CHN)-N-... hydrogen bonds ((HN)-N-... dist. = 2.3-2.5 angstrom) were formed between the azole moieties. Two polymorphs were found for 4-ferrocenyltetrazole, formed with either (CHN)-N-... or pi-pi interactions. (c) 2006 Elsevier B.V. All rights reserved.
• INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3169673B1

  公开（公告）日：2020-04-29