7-bromo-3-ethylheptan-3-ol | 158862-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-bromo-3-ethylheptan-3-ol
• 英文别名: 7-bromo-3-ethylhepta-3-ol
• CAS: 158862-50-1
• 化学式: C₉H₁₉BrO
• 分子量: 223.153
• InChiKey: KKQFKIHPTRDIHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-3-ethylheptan-3-ol 、 N-(3-(diethylamino)propyl)-1-ethyl-4-(3-(4-hydroxy-3-methylphenyl)pentan-3-yl)-1H-pyrrole-2-carboxamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以66%的产率得到N-(3-(diethylamino)propyl)-1-ethyl-4-(3-(4-((5-ethyl-5-hydroxyheptyl)oxy)-3-methylphenyl)pentan-3-yl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Novel Nonsecosteroidal Vitamin D Receptor Modulator Combined with Gemcitabine Enhances Pancreatic Cancer Therapy through Remodeling of the Tumor Microenvironment

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c01197
• 作为产物：
  描述：

  5-溴戊酸乙酯 、 乙基溴化镁 以 四氢呋喃 为溶剂， 以68%的产率得到7-bromo-3-ethylheptan-3-ol
  参考文献：
  名称：

  Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure—Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives

  摘要：

  Vitamin D receptor (VDR) is a nuclear receptor for 1 alpha, 25-dihydroxyvitamin D-3 (1 alpha, 25(OH)(2)D-3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2] octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2] octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.137

文献信息

• NOVEL VITAMIN D ANALOGUES
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S (LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：EP0662953B1

  公开（公告）日：1997-06-18
• US5612325A
  申请人：——

  公开号：US5612325A

  公开（公告）日：1997-03-18
• [EN] NOVEL VITAMIN D ANALOGUES<br/>[FR] NOUVEAUX ANALOGUES DE VITAMINE D
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S (LØVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：WO1994007851A1

  公开（公告）日：1994-04-14

  (EN) The invention relates to compound of formula (I) in which formula R stands for a straight or branched, saturated or unsaturated alkyl group containing from 4 to 12 carbon atoms optionally substituted with a hydroxy group, and possibly containing a ring structure, and in which at least one of the carbon atoms not bearing a hydroxyl group is substituted with one or more halogen atoms or an azido group; and prodrugs of (I) in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups $i(in vivo), in pure form or in mixtures. The compounds show antiinflammatory and immunomodulating effects as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.(FR) Composés de la formule (I) dans laquelle R représente un groupe alkyle linéaire ou ramifié, saturé ou insaturé, contenant de 4 à 12 atomes de carbone éventuellement substitués par un groupe hydroxy, et pouvant contenir une structure cyclique, et dans laquelle au moins un des atomes de carbone ne portant pas un groupe hydroxyle est substitué par un ou plusieurs atomes d'halogène ou un groupe azido. La présente invention concerne également des précurseurs de médicament de la formule (I) dans laquelle un ou plusieurs des groupes hydroxy sont masqués en tant que groupes qui peuvent être reconvertis en groupes hydroxy $i(in vivo), sous forme pure ou de mélanges. Lesdits composés présentent des effets anti-inflammatoires et immunomodulateurs ainsi qu'une forte activité d'induction de la différenciation et d'inhibition de la prolifération indésirable de certaines cellules.
• Novel Nonsecosteroidal Vitamin D Receptor Modulator Combined with Gemcitabine Enhances Pancreatic Cancer Therapy through Remodeling of the Tumor Microenvironment
  作者：Zisheng Kang、Cong Wang、Yu Tong、Yanyi Li、Yi Gao、Siyuan Hou、Meixi Hao、Xiaolin Han、Bin Wang、Qianqian Wang、Can Zhang

  DOI：10.1021/acs.jmedchem.0c01197

  日期：2021.1.14
• Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure—Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives
  作者：Angsuma Wongmayura、Shinya Fujii、Shigeru Ito、Atsushi Kano、Yoshiyuki Taoda、Emiko Kawachi、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1016/j.bmcl.2011.12.137

  日期：2012.2

  Vitamin D receptor (VDR) is a nuclear receptor for 1 alpha, 25-dihydroxyvitamin D-3 (1 alpha, 25(OH)(2)D-3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2] octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2] octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development. (C) 2012 Elsevier Ltd. All rights reserved.