2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile
• 英文别名: 2-(2-amino-3-cyano-6-methoxy-4H-chromen-4-yl)propanedinitrile
• 化学式: C₁₄H₁₀N₄O₂
• 分子量: 266.259
• InChiKey: CNZFIHVBHFKXSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙二腈 、 2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-(2,4-Diamino-3-cyano-6-methoxy-10H-9-oxa-1-aza-anthracen-10-yl)-malononitrile
  参考文献：
  名称：

  Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A class of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2) was discovered. These compounds have demonstrated activity against the enzyme with IC50 values as low as 130 nM and suppress the expression of TNFα in U937 cells. These represent the first small molecule inhibitors of MK-2 to be reported. © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.067
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 丙二腈 在 poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以99%的产率得到2-(2-Amino-3-cyano-6-methoxy-4H-chromen-4-yl)-malononitrile
  参考文献：
  名称：

  One-pot synthesis of 4H-Chromene and Dihydropyrano[3,2-c]chromene derivatives in hydroalcoholic media

  摘要：

  以聚(N,N'-二溴-N-乙基-苯-1,3-二磺酰胺)[PBBS]和 N,N,N',N'-四溴苯-1,3-二磺酰胺[TBBDA]为催化剂，通过简单、温和、高效的程序获得 4H-色烯和二氢吡喃并[3,2-c]色烯，收率从良好到极佳

  DOI：

  10.1590/s0103-50532011000500013

文献信息

• Diethylamine: A smart organocatalyst in eco-safe and diastereoselective synthesis of medicinally privileged 2-amino-4H-chromenes at ambient temperature
  作者：Makarand A. Kulkarni、Kapil S. Pandit、Uday V. Desai、Uday P. Lad、Prakash P. Wadgaonkar

  DOI：10.1016/j.crci.2013.02.016

  日期：2013.8

  Résumé Diethylamine has been demonstrated to be an efficient organocatalyst in the diastereoselective synthesis of Bcl-2 protein antagonist (HA-14-1) and of its structural analogues by one-pot condensation between salicylaldehyde and three different C–H acids, viz. ethyl cyanoacetate, phenylsulfonyl acetonitrile, and malononitrile. Easy commercial availability of the catalyst at extremely low cost and avoidance of conventional work-up as well as purification procedures qualifies this scalable protocol for a “near-ideal synthesis”. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  摘要 二乙胺已被证明是一个高效的有机催化剂，能够以一次性缩合法选择性合成Bcl-2蛋白拮抗剂（HA-14-1）及其结构类似物，该方法通过水杨醛与三种不同的C–H酸（即乙基氰乙酸酯、苯基磺酰乙腈和丙二腈）反应实现。该催化剂在商业上的易得性和极低的成本，以及避免传统的后处理和纯化程序，使这一可扩展的方案符合“近乎理想合成”的标准。 补充材料： 本文的补充材料作为单独文件提供： mmc1.docx
• Chemical entities that kill senescent cells for use in treating age-related disease
  申请人：Unity Biotechnology, Inc.

  公开号：US10195213B2

  公开（公告）日：2019-02-05

  Disclosed herein are compounds that are effective for treatment of various disease states associated with senescence. The disclosed compounds can be used to eliminate senescent cells for disease treatment. The dosing of the compounds includes both single administration and regimens of cycling dosages.

  本文公开的化合物可有效治疗与衰老有关的各种疾病状态。所公开的化合物可用于消除衰老细胞以治疗疾病。化合物的给药方式包括单次给药和循环给药。
• COMPOUNDS AND THERAPEUTIC USES
  申请人：Unity Biotechnology, Inc.

  公开号：US20170281649A1

  公开（公告）日：2017-10-05

  Disclosed herein are compounds that are effective for treatment of various disease states associated with senescence. The disclosed compounds can be used to eliminate senescent cells for disease treatment. The dosing of the compounds includes both single administration and regimens of cycling dosages.
• US6492389B1
  申请人：——

  公开号：US6492389B1

  公开（公告）日：2002-12-10