(+/-)-5-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-pentanoic acid | 911437-67-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-5-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-pentanoic acid
• 英文别名: 5-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)pentanoic acid
• CAS: 911437-67-7
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: BWJFUEKXSSYBAO-UHFFFAOYSA-N

物化性质

• 沸点：
  369.4±17.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-5-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-pentanoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 5-(6-Diazo-5-oxo-hexyl)-2,2-dimethyl-[1,3]dioxolan-4-one
  参考文献：
  名称：

  Exploring alternative Zn-binding groups in the design of HDAC inhibitors: Squaric acid, N-hydroxyurea, and oxazoline analogues of SAHA

  摘要：

  Analogues of suberoylanilide hydroxamic acid (SAHA) were prepared by replacing the Zn-binding group with squaric acid, N-hydroxyurea, and 4-hydroxymethyl oxazoline units, also varying the length of the aliphatic chain. No inhibitory activity on HDAC was observed below 1.0 mu M and no cytotoxic activity on different tumor cell lines was seen below 20.0 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.090
• 作为产物：
  描述：

  DL-2-氨基庚二酸 在 对甲苯磺酸 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (+/-)-5-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)-pentanoic acid
  参考文献：
  名称：

  WO2008/110583

  摘要：

  公开号：

文献信息

• AMIDE COMPOUNDS AND THEIR USE AS ANTITUMOR AGENTS
  申请人：Hanessian Stephan

  公开号：US20100113504A1

  公开（公告）日：2010-05-06

  The present invention relates to a compound of Formula (I), its geometrical isomers, in an optically active form as enantiomers, diastereomers, as well as in the form of racemate, as well as pharmaceutically acceptable salts thereof, wherein R is selected from CONHOH, CONHCH 2 SH, CONHCH 2 SCOCH 3 , SH, SCOCH 3 , SCH 3 , N(OH)COH, COCONHCH 3 and CF 3 for the preparation of a medicament, in particular for selectively inducing terminal differentiation of neoplastic cells and thereby inhibiting proliferation of such cells, for inducing differentiation of tumor cells in a tumor, for inhibiting the activity of histone deacetylase and for the treatment of primary cancer or secondary cancer.

  本发明涉及一种公式(I)的化合物，其几何异构体，以光学活性形式作为对映体，对映异构体，以及盐的形式，其中R选自CONHOH，CONHCH2SH，CONHCH2SCOCH3，SH，SCOCH3，SCH3，N（OH）COH，COCONHCH3和CF3，用于制备药物，特别是用于选择性诱导肿瘤细胞的终端分化，从而抑制这些细胞的增殖，诱导肿瘤中肿瘤细胞的分化，抑制组蛋白去乙酰化酶的活性以及治疗原发性癌症或转移性癌症。
• ω-Alkoxy analogues of SAHA (vorinostat) as inhibitors of HDAC: A study of chain-length and stereochemical dependence
  作者：Stephen Hanessian、Luciana Auzzas、Giuseppe Giannini、Mauro Marzi、Walter Cabri、Marcella Barbarino、Loredana Vesci、Claudio Pisano

  DOI：10.1016/j.bmcl.2007.09.014

  日期：2007.11

  A series of omega-alkoxy ethers were prepared with variation of the length of the aliphatic chain of suberoylanilide hydroxamic acid (SAHA, vorinostat). Eight carbon long chain analogues showed the best activity, among which several substituted benzyl ether derivatives exhibited inhibitory activity on HDAC comparable to SAHA, and antiproliferative activity on three human cell lines (NB4, H460, and HCT-116) better than SAHA. However, no significant difference in antiproliferative activity was observed between two enantiomers bearing the benzyl ether moiety. (C) 2007 Published by Elsevier Ltd.
• [EN] AMIDE COMPOUNDS AND THEIR USE AS ANTITUMOR AGENTS<br/>[FR] COMPOSÉS AMIDES ET LEUR UTILISATION COMME AGENTS ANTI-TUMORAUX
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2008110583A1

  公开（公告）日：2008-09-18

  [EN] The present invention relates to a compound of Formula (I), its geometrical isomers, in an optically active form as enantiomers, diastereomers, as well as in the form of racemate, as well as pharmaceutically acceptable salts thereof, wherein R is selected from CONHOH, CONHCH₂SH, CONHCH₂SCOCH₃, SH, SCOCH₃, SCH₃, N(OH)COH, COCONHCH₃ and CF₃for the preparation of a medicament, in particular for for selectively inducing terminal differentiation of neoplastic cells and thereby inhibiting proliferation of such cells, for inducing differentiation of tumor cells in a tumor, for inhibiting the activity of histone deacetylase and for the treatment of primary cancer or secondary cancer.
  [FR] La présente invention porte sur un composé de Formule (I), sur ses isomères géométriques, dans une forme optiquement active comme énantiomères, diastéréisomères ainsi que dans la forme de racémates, ainsi que sur leurs sels pharmaceutiquement acceptables. Dans la formule, R est choisi parmi CONHOH, CONHCH₂SH, CONHCH₂SCOCH₃, SH, SCOCH₃, SCH₃, N(OH)COH, COCONHCH₃ et CF₃ pour la préparation d'un médicament, en particulier pour induire de façon sélective une différenciation terminale de cellules néoplasiques et, de ce fait, pour inhiber la prolifération de telles cellules, pour induire une différenciation de cellules tumorales dans une tumeur, pour inhiber l'activité de l'histone désacétylase et pour le traitement d'un cancer primaire ou d'un cancer secondaire.
• Exploring alternative Zn-binding groups in the design of HDAC inhibitors: Squaric acid, N-hydroxyurea, and oxazoline analogues of SAHA
  作者：Stephen Hanessian、Valerio Vinci、Luciana Auzzas、Mauro Marzi、Giuseppe Giannini

  DOI：10.1016/j.bmcl.2006.06.090

  日期：2006.9

  Analogues of suberoylanilide hydroxamic acid (SAHA) were prepared by replacing the Zn-binding group with squaric acid, N-hydroxyurea, and 4-hydroxymethyl oxazoline units, also varying the length of the aliphatic chain. No inhibitory activity on HDAC was observed below 1.0 mu M and no cytotoxic activity on different tumor cell lines was seen below 20.0 mu M. (c) 2006 Elsevier Ltd. All rights reserved.
• WO2008/110583
  申请人：——

  公开号：——

  公开（公告）日：——