2-[6-(2,3-dihydro-1H-indol-1-yl)-6-oxohexyl]-1H-isoindole-1,3(2H)-dione | 97125-02-5

• 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-(2,3-dihydro-1H-indol-1-yl)-6-oxohexyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[6-(2,3-dihydroindol-1-yl)-6-oxohexyl]isoindole-1,3-dione
• CAS: 97125-02-5
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: SNKJLVMFPQVHKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[6-(2,3-dihydro-1H-indol-1-yl)-6-oxohexyl]-1H-isoindole-1,3(2H)-dione 在 lithium aluminium tetrahydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 22.0h， 生成
  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：

  6-氯己酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 2-[6-(2,3-dihydro-1H-indol-1-yl)-6-oxohexyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  硫鎓中间体中 E/Z 选择性的 DFT 预测指导的酰胺的直接对映选择性 α-胺化

  摘要：

  手性胺是一类非常重要的化合物，对其强大的合成方法仍然有很高的需求。在此，我们报告了一种前所未有的从廉价且丰富的起始原料制备手性 α-氨基酰胺的方法。我们的策略依赖于使用对映体纯亚磺酰胺对酰胺进行直接胺化。它涉及关键硫鎓中间体的 [2,3]-σ 重排。我们进一步展示了量子化学计算如何允许对这种氨基-乙烯氧基-硫鎓物种的关键E/Z选择性进行预测性洞察。

  DOI：

  10.1016/j.chempr.2023.03.002

文献信息

• NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND METHODS FOR USE OF THE SAME
  申请人：THE TRUSTEES OF INDIANA UNIVERSITY

  公开号：US20210070784A1

  公开（公告）日：2021-03-11

  Disclosed herein are compounds that can act as inhibitors of nicotinamide phosphoribosyltransferase (“NAMPT”), and methods for their use in treating or preventing diseases, such as pulmonary arterial hypertension (“PAH”). The compounds described herein can include compounds of Formula (II) and pharmaceutically acceptable salts thereof: wherein the substituents are as described.
• [EN] NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE INHIBITORS AND METHODS FOR USE OF THE SAME<br/>[FR] INHIBITEURS DE LA NICOTINAMIDE PHOSPHORIBOSYLTRANSFÉRASE ET MÉTHODES D'UTILISATION DE CEUX-CI
  申请人：THE BOARO OF TRUSTEES OF THE UNIV OF ILLINOIS

  公开号：WO2019153007A2

  公开（公告）日：2019-08-08

  Disclosed herein are compounds that can act as inhibitors of nicotinamide phosphoribosyltransferase ("NAMPT"), and methods for their use in treating or preventing diseases, such as pulmonary arterial hypertension ("PAH"). The compounds described herein can include compounds of Formula (II) and pharmaceutically acceptable salts thereof: wherein the substituents are as described.
• Structure-activity relationships among di- and tetramine disulfides related to benextramine
  作者：M. Alvarez、R. Granados、D. Mauleon、G. Rosell、M. Salas、J. Salles、N. Valls

  DOI：10.1021/jm00390a011

  日期：1987.7

  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.
• Direct enantioselective α-amination of amides guided by DFT prediction of E/Z selectivity in a sulfonium intermediate
  作者：Minghao Feng、Anthony J. Fernandes、Ricardo Meyrelles、Nuno Maulide

  DOI：10.1016/j.chempr.2023.03.002

  日期：2023.3

  method for the preparation of chiral α-amino amides from cheap and abundant starting materials. Our strategy relies on a direct amination of amides using enantiopure sulfinamides. It involves a [2,3]-sigmatropic rearrangement of a key sulfonium intermediate. We further show how quantum chemical calculations allow predictive insights into the critical E/Z selectivity of this amino-vinyloxy-sulfonium species

  手性胺是一类非常重要的化合物，对其强大的合成方法仍然有很高的需求。在此，我们报告了一种前所未有的从廉价且丰富的起始原料制备手性 α-氨基酰胺的方法。我们的策略依赖于使用对映体纯亚磺酰胺对酰胺进行直接胺化。它涉及关键硫鎓中间体的 [2,3]-σ 重排。我们进一步展示了量子化学计算如何允许对这种氨基-乙烯氧基-硫鎓物种的关键E/Z选择性进行预测性洞察。