3-hydroxypiperidin-1-ylacetonitrile | 857636-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-hydroxypiperidin-1-ylacetonitrile
• 英文别名: 3-hydroxy-piperidin-1-yl-acetonitrile；2-(3-Hydroxypiperidin-1-YL)acetonitrile
• CAS: 857636-97-6
• 化学式: C₇H₁₂N₂O
• mdl: MFCD09745369
• 分子量: 140.185
• InChiKey: FGVSVENNNSZEBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxypiperidin-1-ylacetonitrile 在 氮气 、 水 、 sodium hydroxide 、 乙酸乙酯 、 氢氧化锂 、 水铝矿 、 二氯甲烷 、 magnesium sulfate 作用下， 以 四氢呋喃 为溶剂， 172.0 ℃ 、666.61 Pa 条件下， 反应 5.25h， 以obtained as a straw coloured oil (1.95 g, 63%)的产率得到1-(2-氨基乙基)-3-哌啶醇
  参考文献：
  名称：

  Antharquinone Compounds as Anti Cancer Compounds

  摘要：

  通式（I）或其盐（式I）的蒽醌化合物，其中R1至R4均选自H、C1-4烷基、X1、-NHR0N（Rs）2的群，其中R°是C1l12烷二基，每个R5是H或可选取代的C14烷基，以及式（II）的一组，其中至少有一个R6、R7和R8选自X2和X2取代的C1-4烷基，其余为H或C14烷基；R9选自H、C14烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1.6烷氧基、芳基氧基或酰氧基；X2为卤素原子、羟基、C16烷氧基、芳基氧基或酰氧基；前提是至少有一个R1至R4是式（II）的一组。N-氧化物是有用的前药，在低氧肿瘤中选择性地生物还原为相应的环状胺衍生物。胺化合物具有细胞毒性，并可用作具有拓扑异构酶II抑制活性的烷基化剂，用于癌症治疗。

  公开号：

  US20080027107A1
• 作为产物：
  描述：

  3-羟基哌啶 、 溴乙腈 以 四氢呋喃 为溶剂， 反应 0.5h， 以83%的产率得到3-hydroxypiperidin-1-ylacetonitrile
  参考文献：
  名称：

  [EN] ANTHARQUINONE COMPOUNDS AS ANTI CANCER COMPOUNDS
  [FR] UTILISATION DE COMPOSES D'ANTHRAQUINONE EN TANT QUE COMPOSES ANTICANCEREUX

  摘要：

  通式（I）的蒽醌化合物或其盐（公式I），其中R1至R4分别选自H、C1-4烷基、X1、-NHR0N（R5）2，其中R0为C1-12烷二基，每个R5为H或可选择性取代的C1-4烷基，以及公式（II）中的一组，其中R6、R7和R8中至少有一个选自X2，和X2取代的C1-4烷基，其他为H或C1-4烷基；R9选自H、C1-4烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1-6烷氧基、芳基氧基或酰氧基；X2为卤素原子、羟基、C1-6烷氧基、芳基氧基或酰氧基；前提是R1至R4中至少有一个是公式（II）的一组。N-氧化物是有用的前药，可选择性地在低氧肿瘤中生物还原为相应的环胺衍生物。胺化合物具有细胞毒性，可用作在癌症治疗中具有拓扑异构酶II抑制活性的烷基化剂。

  公开号：

  WO2005061453A1

文献信息

• [EN] ANTHARQUINONE COMPOUNDS AS ANTI CANCER COMPOUNDS<br/>[FR] UTILISATION DE COMPOSES D'ANTHRAQUINONE EN TANT QUE COMPOSES ANTICANCEREUX
  申请人：UNIV LONDON PHARMACY

  公开号：WO2005061453A1

  公开（公告）日：2005-07-07

  Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R1 to R4 are each selected from the group consisting of H, C1-4 alkyl, X1, -NHR0N (R5)2 in which R0 is a C1-12 alkanediyl and each R5 is H or optionally substituted C1-4 alkyl, and a group of formula (II) in which at least one of R6,R7 and R8 is selected from X2 , and X2 substituted C1-4 alkyl and any others are H or C1-4 alkyl; R9 is selected from H, C1-4 alkyl, X2 and X2 substituted C1-4 alkyl; m is 0 or 1; n is 1 or 2; X1 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; and X2 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R1 to R4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.

  通式（I）的蒽醌化合物或其盐（公式I），其中R1至R4分别选自H、C1-4烷基、X1、-NHR0N（R5）2，其中R0为C1-12烷二基，每个R5为H或可选择性取代的C1-4烷基，以及公式（II）中的一组，其中R6、R7和R8中至少有一个选自X2，和X2取代的C1-4烷基，其他为H或C1-4烷基；R9选自H、C1-4烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1-6烷氧基、芳基氧基或酰氧基；X2为卤素原子、羟基、C1-6烷氧基、芳基氧基或酰氧基；前提是R1至R4中至少有一个是公式（II）的一组。N-氧化物是有用的前药，可选择性地在低氧肿瘤中生物还原为相应的环胺衍生物。胺化合物具有细胞毒性，可用作在癌症治疗中具有拓扑异构酶II抑制活性的烷基化剂。
• Antharquinone Compounds as Anti Cancer Compounds
  申请人：Patterson Laurence Hylton

  公开号：US20080027107A1

  公开（公告）日：2008-01-31

  Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R 1 to R 4 are each selected from the group consisting of H, C 1-4 alkyl, X 1 , —NHR 0 N (Rs)2 in which R° is a C 1 l 12 alkanediyl and each R 5 is H or optionally substituted C 14 alkyl, and a group of formula (11) in which at least one of R 6 ,R 7 and R 8 is selected from X 2 , and X 2 substituted C 1-4 alkyl and any others are H or C 14 alkyl; R 9 is selected from H, C 1 4 alkyl, X 2 and X 2 substituted C 1-4 alkyl; m is 0 or 1; n is 1 or 2; X 1 is a halogen atom, a hydroxyl group, a C 1 . 6 alkoxyl group, an aryloxy group or an acyloxy group; and X 2 is a halogen atom, a hydroxyl group, a C 1 6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R 1 to R 4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.

  通式（I）或其盐（式I）的蒽醌化合物，其中R1至R4均选自H、C1-4烷基、X1、-NHR0N（Rs）2的群，其中R°是C1l12烷二基，每个R5是H或可选取代的C14烷基，以及式（II）的一组，其中至少有一个R6、R7和R8选自X2和X2取代的C1-4烷基，其余为H或C14烷基；R9选自H、C14烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1.6烷氧基、芳基氧基或酰氧基；X2为卤素原子、羟基、C16烷氧基、芳基氧基或酰氧基；前提是至少有一个R1至R4是式（II）的一组。N-氧化物是有用的前药，在低氧肿瘤中选择性地生物还原为相应的环状胺衍生物。胺化合物具有细胞毒性，并可用作具有拓扑异构酶II抑制活性的烷基化剂，用于癌症治疗。
• Anthraquinone compounds as anti cancer compounds
  申请人：Somanta Limited

  公开号：US07557215B2

  公开（公告）日：2009-07-07

  Anthraquinone compounds of the general formula (I) or a salt thereof (Formula I) in which R1 to R4 are each selected from the group consisting of H, C1-4 alkyl, X1, —NHR0N (R5)2 in which R0 is a C1-12 alkanediyl and each R5 is H or optionally substituted C1-4 alkyl, and a group of formula (II) in which at least one of R6, R7 and R8 is selected from X2, and X2 substituted C1-4 alkyl and any others are H or C1-4 alkyl; R9 is selected from H, C1-4 alkyl, X2 and X2 substituted C1-4 alkyl; m is 0 or 1; n is 1 or 2; X1 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; and X2 is a halogen atom, a hydroxyl group, a C1-6 alkoxyl group, an aryloxy group or an acyloxy group; provided that at least one of R1 to R4 is a group of formula (II). The N-oxides are useful prodrugs which are selectively bioreduced in hypoxic tumours to the corresponding cyclic amine derivatives. The amine compounds are cytotoxic and may be used as alkylating agents having topoisomerase II inhibiting activities in cancer therapy.

  通式（I）或其盐（式I）的蒽醌类化合物，其中R1至R4分别选自H、C1-4烷基、X1、-NHR0N（R5）2，其中R0为C1-12烷二基，每个R5为H或可选取代的C1-4烷基，以及公式（II）的基团，其中至少有一个R6、R7和R8选自X2和X2取代的C1-4烷基，其余为H或C1-4烷基；R9选自H、C1-4烷基、X2和X2取代的C1-4烷基；m为0或1；n为1或2；X1为卤素原子、羟基、C1-6烷氧基、芳氧基或酰氧基；X2为卤素原子、羟基、C1-6烷氧基、芳氧基或酰氧基；但要求R1至R4中至少有一个是公式（II）的基团。N-氧化物是有用的前药，可在低氧肿瘤中选择性地生物还原为相应的环状胺衍生物。胺类化合物具有细胞毒性，并可用作具有拓扑异构酶II抑制活性的烷基化剂在癌症治疗中使用。
• Development of Nonsymmetrical 1,4-Disubstituted Anthraquinones That Are Potently Active against Cisplatin-Resistant Ovarian Cancer Cells
  作者：Klaus Pors、Jane A. Plumb、Robert Brown、Paul Teesdale-Spittle、Mark Searcey、Paul J. Smith、Laurence H. Patterson

  DOI：10.1021/jm050438f

  日期：2005.10.1

  A novel series of 1,4-disubstituted aminoanthraquinones were prepared by ipso-displacement of 1,4-difluoro-5,8-dihydroxyanthraquinones by hydroxylated piperidinyl- or pyrrolidinylalkyl-amino side chains. One aminoanthraquinone (13) was further derivatized to a chloropropylamino analogue by treatment with triphenylphosphine-carbon tetrachloride. The compounds were evaluated in the A2780 ovarian cancer cell line and its cisplatin-resistant variants (A2780/cp70 and A2780/MCP1). The novel anthraquinones were shown to possess up to 5-fold increased potency against the cisplatin-resistant cells compared to the wild-type cells. Growth curve analysis of the hydroxyethylaminoanthraquinone 8 in the osteosarcoma cell line U-2 OS showed that the cell cycle is not frozen, rather there is a late cell cycle arrest consistent with the action of a DNA-damaging topoisomerase II inhibitor. Accumulative apoptotic events, using time lapse photography, indicate that 8 is capable of fully engaging cell cycle arrest pathways in G2 in the absence of early apoptotic commitment. 8 and its chloropropyl analogue 13 retained significant activity against human A2780/cp70 xenografted tumors in mice.
• [EN] SMALL MOLECULE INHIBITORS OF TDP-43 ACTIVITY AND USES THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITRICES DE L'ACTIVITÉ DE TDP-43 ET LEURS UTILISATIONS
  申请人：UNIV ARIZONA

  公开号：WO2022015997A3

  公开（公告）日：2022-02-24