2-(6-benzyloxyhexyl)isoindoline-1,3-dione | 108296-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(6-benzyloxyhexyl)isoindoline-1,3-dione
• 英文别名: 2-(6-(Benzyloxy)hexyl)isoindoline-1,3-dione；2-(6-phenylmethoxyhexyl)isoindole-1,3-dione
• CAS: 108296-25-9
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: WBFNMGSFDBBBPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(6-benzyloxyhexyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 6.0h， 生成 2-(6-Benzyloxy-hexylamino)-ethanethiol
  参考文献：
  名称：

  Structure-activity relationships among di- and tetramine disulfides related to benextramine

  摘要：

  The synthesis and irreversible alpha-blocking activity in the rat vas deferens of a series of tetra- and diamine disulfides 2-38, structural analogues of benextramine (BHC), are described. All compounds containing a central cystamine moiety displayed an irreversible alpha-adrenergic blockade at concentrations ranging from 10(-4) to 6 X 10(-6)M. Potency was increased in cystamines N,N'-disubstituted with 6-aminohexyl groups, especially when the outer nitrogen atoms bear arylalkyl substituents or are enclosed in a ring. However, N,N,N',N'-tetrasubstituted cystamines were poor blockers. Structural specificity in the outer portion of the tetramine disulfide is low, since many types of substituents gave rise to potent alpha-blockers. Even replacement of the outer amines with nonbasic ethers or amides was observed to maintain irreversible alpha-blockade.

  DOI：

  10.1021/jm00390a011
• 作为产物：
  描述：

  1,6-二溴己烷 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 2-(6-benzyloxyhexyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Structure-activity relationships among di- and tetramine disulfides related to benextramine

  摘要：

  The synthesis and irreversible alpha-blocking activity in the rat vas deferens of a series of tetra- and diamine disulfides 2-38, structural analogues of benextramine (BHC), are described. All compounds containing a central cystamine moiety displayed an irreversible alpha-adrenergic blockade at concentrations ranging from 10(-4) to 6 X 10(-6)M. Potency was increased in cystamines N,N'-disubstituted with 6-aminohexyl groups, especially when the outer nitrogen atoms bear arylalkyl substituents or are enclosed in a ring. However, N,N,N',N'-tetrasubstituted cystamines were poor blockers. Structural specificity in the outer portion of the tetramine disulfide is low, since many types of substituents gave rise to potent alpha-blockers. Even replacement of the outer amines with nonbasic ethers or amides was observed to maintain irreversible alpha-blockade.

  DOI：

  10.1021/jm00390a011

文献信息

• [EN] GalNAc CLUSTER PHOSPHORAMIDITE<br/>[FR] AGRÉGAT DE GALNAC-PHOSPHORAMIDITE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017084987A1

  公开（公告）日：2017-05-26

  The invention comprises Gal NAc phosphoramidite derivatives of the formula (I), wherein R1 is a hydroxy protecting group, n is an integer from 0 to 10 and m is an integer from 0 to 20 and its corresponding enantiomers and/ or optical isomers thereof. The invention further comprises a process for the preparation of the Gal NAc phosphoramidite derivatives of the formula (I) and its use in the preparation of therapeutically valuable GalNAc-cluster oligonucleotide conjugates.

  该发明包括公式（I）中的Gal NAc磷酰胺衍生物，其中R1是一个羟基保护基团，n是从0到10的整数，m是从0到20的整数，以及其相应的对映体和/或光学异构体。该发明还包括一种制备公式（I）中的Gal NAc磷酰胺衍生物的方法，以及其在制备具有治疗价值的GalNAc-簇寡核苷酸共轭物中的用途。
• Galnac cluster phosphoramidite
  申请人：Hoffmann-La Roche Inc.

  公开号：US10590156B2

  公开（公告）日：2020-03-17

  The invention comprises GalNAc phosphoramidite derivatives of the formula I wherein R1 is a hydroxy protecting group, n is an integer from 0 to 10 and m is an integer from 0 to 20 and its corresponding enantiomers and/or optical isomers thereof. The invention further comprises a process for the preparation of the GalNAc phosphoramidite derivatives of the formula I and its use in the preparation of therapeutically valuable GalNAc-cluster oligonucleotide conjugates.

  本发明包括式 I 的 GalNAc 亚磷酰胺衍生物 其中 R1 是羟基保护基团，n 是 0 至 10 的整数，m 是 0 至 20 的整数及其相应的对映体和/或光学异构体。本发明还包括制备式 I 的 GalNAc 亚磷酰胺衍生物的工艺及其在制备具有治疗价值的 GalNAc 簇寡核苷酸共轭物中的用途。
• ALVAREZ, M.;MAULEON, D.;PUJOL, M. D.;ROSELL, G.;SALAS, M. L., AN. QUIM. REAL. SOC. ESP. QUIM., 83,(1987) N 2, 155-161
  作者：ALVAREZ, M.、MAULEON, D.、PUJOL, M. D.、ROSELL, G.、SALAS, M. L.

  DOI：——

  日期：——
• GalNAc CLUSTER PHOSPHORAMIDITE
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3377510A1

  公开（公告）日：2018-09-26
• GALNAC CLUSTER PHOSPHORAMIDITE
  申请人：F. Hoffmann-La Roche AG

  公开号：EP3377510B1

  公开（公告）日：2020-12-02