1-bromo-3-ethylpentan-3-ol | 210219-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-3-ethylpentan-3-ol
• 英文别名: 5-Bromo-3-ethyl-3-pentanol
• CAS: 210219-74-2
• 化学式: C₇H₁₅BrO
• 分子量: 195.1
• InChiKey: ACWCGDGCBASRKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  4
• 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：

  1-bromo-3-ethylpentan-3-ol 在 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.0h， 生成 N-(3-(dimethylamino)propyl)-1-ethyl-5-(3-(4-((3-ethyl-3-hydroxypentyl)oxy)-3-methylphenyl)pentan-3-yl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Further Developments of the Phenyl-Pyrrolyl Pentane Series of Nonsteroidal Vitamin D Receptor Modulators as Anticancer Agents

  摘要：

  The vitamin D (3) receptor (VDR), which belongs to the nuclear-receptor superfamily, is a potential molecular target for anticancer-drug discovery. In this study, a series of nonsteroidal vitamin D mimics with phenyl-pyrrolyl pentane skeletons with therapeutic potentials in cancer treatment were synthesized. Among them, 11b and 11g were identified as the most effective agents in reducing the viability of four cancer-cell lines, particularly those of breast-cancer cells, with IC50 values in the submicromolar-concentration range. In addition, 11b and 11g possessed VDR-binding affinities and displayed significant partial VDR-agonistic activities determined by dual-luciferase-reporter assays and human-leukemia-cell-line (HL-60)-differentiation assays. Furthermore, 11b and 11g inhibited tumor growth in an orthotopic breast-tumor model via inhibition of cell proliferation and induction of cell apoptosis. More importantly, 11b and 11g exhibited favorable pharmacokinetic behavior in vivo and did not increase serum calcium levels or cause any other apparent side effects. In summary, 11b and 11g act as novel VDR modulators and may be promising candidates for cancer chemotherapy.

  DOI：

  10.1021/acs.jmedchem.8b00106
• 作为产物：
  描述：

  溴乙烷 、 3-溴丙酸甲酯 在 碘 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以43%的产率得到1-bromo-3-ethylpentan-3-ol
  参考文献：
  名称：

  Further Developments of the Phenyl-Pyrrolyl Pentane Series of Nonsteroidal Vitamin D Receptor Modulators as Anticancer Agents

  摘要：

  The vitamin D (3) receptor (VDR), which belongs to the nuclear-receptor superfamily, is a potential molecular target for anticancer-drug discovery. In this study, a series of nonsteroidal vitamin D mimics with phenyl-pyrrolyl pentane skeletons with therapeutic potentials in cancer treatment were synthesized. Among them, 11b and 11g were identified as the most effective agents in reducing the viability of four cancer-cell lines, particularly those of breast-cancer cells, with IC50 values in the submicromolar-concentration range. In addition, 11b and 11g possessed VDR-binding affinities and displayed significant partial VDR-agonistic activities determined by dual-luciferase-reporter assays and human-leukemia-cell-line (HL-60)-differentiation assays. Furthermore, 11b and 11g inhibited tumor growth in an orthotopic breast-tumor model via inhibition of cell proliferation and induction of cell apoptosis. More importantly, 11b and 11g exhibited favorable pharmacokinetic behavior in vivo and did not increase serum calcium levels or cause any other apparent side effects. In summary, 11b and 11g act as novel VDR modulators and may be promising candidates for cancer chemotherapy.

  DOI：

  10.1021/acs.jmedchem.8b00106

文献信息

• Vitamin d derivatives
  申请人：——

  公开号：US20030195176A1

  公开（公告）日：2003-10-16

  The object of the present invention is to provide a vitamin D derivative exhibiting excellent physiological activity as medicines, in particular as therapeutic agents for skin disease including psoriasis, and having decreased hypercalcemic activity. The present invention provides vitamin D derivatives represented by the general Formula ( 1 ): 1 wherein in Formula ( 1 ), X is oxygen or sulfur; R 1 is hydrogen or Formula ( 2 ) 2 R 2 is hydrogen or alkyl; R 3 and R 4 are hydrogen or alkyl or R 3 and R 4 together form a double bond between the 16 - and 17 -positions; R 5 is hydrogen or -OR 13 in which R 13 is hydrogen or a protecting group; and R 6 is hydrogen or a protecting group.

  本发明的目的是提供一种表现出优异生理活性的维生素D衍生物作为药物，特别是作为治疗包括牛皮癣在内的皮肤疾病的药剂，并且具有降低的高钙血症活性。 本发明提供了由通式（1）表示的维生素D衍生物： 其中在通式（1）中，X为氧或硫； R1为氢或通式（2）； R2为氢或烷基； R3和R4为氢或烷基，或者R3和R4共同形成16-和17-位置之间的双键； R5为氢或-OR13，其中R13为氢或保护基；以及 R6为氢或保护基。
• 16-ENE-VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020193616A1

  公开（公告）日：2002-12-19

  The compound of the formula (24): 1 wherein R 9 R 10 may be the same or different and each represent a hydrogen atom or a protecting group.

  化学式（24）的化合物：其中R9和R10可以相同或不同，且均表示氢原子或保护基。
• 16-ene-vitamin D derivatives
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：US20020032340A1

  公开（公告）日：2002-03-14

  A compound having the formula (4): wherein 1 X is oxygen or sulfur, R 9 and R 10 are each a hydrogen or a protecting group, and R 11 is an aliphatic hydrocarbon, a —COR 12 group where R 12 is alkyl, aryl or alkoxy, or a group of formula 2 wherein R 5 and R 6 are each hydrogen or hydroxyl, m is 1 to 4, and n is 0-2.

  一个化合物的化学式为(4)，其中1X是氧或硫，R9和R10分别是氢或保护基团，R11是脂肪烃、—COR12基团（其中R12是烷基、芳基或烷氧基）或化学式2中的基团（其中R5和R6分别是氢或羟基，m为1到4，n为0-2）。
• 16-ENE-vitamin D derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06555699B2

  公开（公告）日：2003-04-29

  The compound of the formula (24): wherein R9 and R10 may be the same or different and each represent a hydrogen atom or a protecting group.

  公式（24）的化合物：其中R9和R10可以相同也可以不同，每个代表氢原子或保护基团。
• VITAMIN D DERIVATIVES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1275643A1

  公开（公告）日：2003-01-15

  The object of the present invention is to provide a vitamin D derivative exhibiting excellent physiological activity as medicines, in particular as therapeutic agents for skin disease including psoriasis, and having decreased hypercalcemic activity. The present invention provides vitamin D derivatives represented by the general Formula (1):    wherein in Formula (1), X is oxygen or sulfur; R1 is hydrogen or Formula (2) R2 is hydrogen or alkyl; R3 and R4 are hydrogen or alkyl or R3 and R4 together form a double bond between the 16- and 17-positions; R5 is hydrogen or -OR13 in which R13 is hydrogen or a protecting group; and R6 is hydrogen or a protecting group.

  本发明的目的是提供一种维生素 D 衍生物，该衍生物作为药物，特别是作为包括牛皮癣在内的皮肤病的治疗药物，具有优异的生理活性，并且具有降低高钙血症的活性。 本发明提供通式（1）所代表的维生素 D 衍生物： 其中 式（1）中，X 是氧或硫； R1 是氢或式（2） R2 是氢或烷基 R3 和 R4 是氢或烷基，或 R3 和 R4 一起在 16 位和 17 位之间形成双键； R5 是氢或-OR13，其中 R13 是氢或保护基；以及 R6 是氢或保护基团。