4-(dimethylamino)pyridine-2,6-dicarbaldehyde | 153504-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(dimethylamino)pyridine-2,6-dicarbaldehyde
• CAS: 153504-00-8
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: YBQMKZYLFDZKKV-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±42.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(dimethylamino)pyridine-2,6-dicarbaldehyde 在 盐酸 、 甲醇 、 3-甲基吲哚 、 sodium cyanoborohydride 、 溶剂黄146 、 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 3-[[4-(Dimethylamino)-6-[(3-sulfanylpropylamino)methyl]-2-pyridyl]methylamino]propane-1-thiol
  参考文献：
  名称：

  锌指蛋白HIV-EP1的金属螯合抑制剂。通过引入SH基团显着增强抑制活性。

  摘要：

  HIV-EP1是一种C2H2型锌指蛋白，可与HIV前病毒的长末端重复序列中存在的DNA kappa B位点结合。以前我们已经报道了具有组氨酸-吡啶-组氨酸骨架的锌螯合剂，并且通过从锌指结构域中去除锌而成功抑制了HIV-EP1的DNA结合。为了增强我们先前的锌螯合剂的抑制活性，本文合成了包含吡啶和氨基链烷硫醇的新型螯合剂。这些显示出对HIV-EP1的DNA结合的显着抑制活性。尤其是其中一个具有双（2-巯基乙基）氨基侧链的化合物，其抑制活性（IC50，约4 microM）比我们之前报道的最强抑制剂强10倍。

  DOI：

  10.1021/jm950831t
• 作为产物：
  描述：

  4-(dimethylamino)picolinaldehyde 在 盐酸 、 三氟化硼乙醚 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 53.0h， 生成 4-(dimethylamino)pyridine-2,6-dicarbaldehyde
  参考文献：
  名称：

  Novel metal chelating molecules with anticancer activity. Striking effect of the imidazole substitution of the histidine–pyridine–histidine system

  摘要：

  Previously we have reported a metal chelating histidine-pyridine-histidine system possessing a trityl group on the histidine imidazole, namely HPH-2Trt, which induces apoptosis in human pancreatic adenocarcinoma AsPC-1 cells. Herein the influence of the imidazole substitution of HPH-2Trt was examined. Five related compounds, HPH-1Trt, HPH-2Bzl, HPH-1Bzl, HPH-2Me, and HPH-1Me were newly synthesized and screened for their activity against AsPC-1 and brain tumor cells U87 and U251. HPH-1Trt and HPH-2Trt were highly active among the tested HPH compounds. In vitro DNA cleavage assay showed both HPH-1Trt and HPH-2Trt completely disintegrate pUC19 DNA. The introduction of trityl group decisively potentiated the activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.044

文献信息

• Synthetic inhibitors of regulatory proteins involved in the signaling pathway of the replication of human immunodeficiency virus 1
  作者：Masami Otsuka、Mikako Fujita、Yukio Sugiura、Tadashi Yamamoto、Jun-ichiro Inoue、Toshio Maekawa、Shunsuke Ishii

  DOI：10.1016/s0968-0896(96)00203-9

  日期：1997.1

  NF-kappa B, HIV-EP1, Sp1, and E1A are transcriptional proteins involved in the long terminal repeat-directed expression of HIV-1. The inhibitory effect of 18 dimethylaminopyridine-based compounds against these regulatory proteins was studied. Experiments using NF-kappa B-beads showed that histidine-pyridine-histidine compounds and their zinc complexes are inhibitory not only for the NF-kappa B-DNA binding, but also for the binding of NF-KB with the inhibitory protein I kappa B. Discriminative inhibition of the DNA binding of two distinct C2H2 type zinc finger proteins HIV-EP1 and Sp1 was also attempted using the synthetic compounds. Whereas some compounds inhibited the DNA binding of both HIV-EP1 and Sp1 at 300 mu M, others preferentially and completely inhibited HIV-EP1 without much suppression of Sp1. Mercapto compounds were more potent and uniformly inhibitory against both HIV-EP1 and Sp1 at 30 mu M. Disulfide compounds were also remarkably inhibitory against HIV-EP1 and Sp1 also at 30 mu M whereas the shorter-chain disulfides 7 and 9 were effective only for HIV-EP1. S-Alkyl derivatives preferentially inhibited HIV-EP1 at 300 mu M. The dimethylamino compound was the sole compound inhibitory only against Sp1, being non-inhibitory against HIV-EP1. Relevant combinations of these inhibitors would allow us to inhibit NF-kappa B, HIV-EP1, and Sp1 in any combinations. Inhibition of the TBP binding of C-4 type zinc finger protein adenovirus E1A was also examined. It was found that two compounds induced, at 50 mM concentration, effective inhibition of the TBP binding of E1A, demonstrating that it is possible in principle to inhibit the protein-protein interaction of zinc finger proteins. Copyright (C) 1997 Elsevier Science Ltd.
• JP2016/160223
  申请人：——

  公开号：——

  公开（公告）日：——
• Restructuring of the bleomycin metal core. Novel oxygen-activating ligands with symmetrized structure
  作者：Masami Otsuka、Honoo Satake、Yukio Sugiura、Satoru Murakami、Masakatsu Shibasaki、Susumu Kobayashi

  DOI：10.1016/s0040-4039(00)61368-0

  日期：——

  Novel ligands having symmetrized coordination environment consisting of two histidine units and a pyridine are prepared. Oxygen activating efficiency of the iron complexes of the synthetic ligands increases by introducing electron donating substituent into the pyridine ring.
• Metal-Chelating Inhibitors of a Zinc Finger Protein HIV-EP1. Remarkable Potentiation of Inhibitory Activity by Introduction of SH Groups
  作者：Mikako Fujita、Masami Otsuka、Yukio Sugiura

  DOI：10.1021/jm950831t

  日期：1996.1.1

  HIV-EP1 is a C2H2 type zinc finger protein which binds to DNA kappa B site present in the long terminal repeat of HIV provirus. Previously we have reported zinc chelators having histidine--pyridine--histidine skeleton and were successful in inhibiting the DNA binding of HIV-EP1 by removing zinc from the zinc finger domain. Aiming at the potentiation of the inhibitory activity of our previous zinc chelators

  HIV-EP1是一种C2H2型锌指蛋白，可与HIV前病毒的长末端重复序列中存在的DNA kappa B位点结合。以前我们已经报道了具有组氨酸-吡啶-组氨酸骨架的锌螯合剂，并且通过从锌指结构域中去除锌而成功抑制了HIV-EP1的DNA结合。为了增强我们先前的锌螯合剂的抑制活性，本文合成了包含吡啶和氨基链烷硫醇的新型螯合剂。这些显示出对HIV-EP1的DNA结合的显着抑制活性。尤其是其中一个具有双（2-巯基乙基）氨基侧链的化合物，其抑制活性（IC50，约4 microM）比我们之前报道的最强抑制剂强10倍。
• Novel metal chelating molecules with anticancer activity. Striking effect of the imidazole substitution of the histidine–pyridine–histidine system
  作者：Taha F.S. Ali、Kana Iwamaru、Halil Ibrahim Ciftci、Ryoko Koga、Masahiro Matsumoto、Yasunori Oba、Hiromasa Kurosaki、Mikako Fujita、Yoshinari Okamoto、Kazuo Umezawa、Mitsuyoshi Nakao、Takuichiro Hide、Keishi Makino、Jun-ichi Kuratsu、Mohamed Abdel-Aziz、Gamal El-Din A.A. Abuo-Rahma、Eman A.M. Beshr、Masami Otsuka

  DOI：10.1016/j.bmc.2015.07.044

  日期：2015.9

  Previously we have reported a metal chelating histidine-pyridine-histidine system possessing a trityl group on the histidine imidazole, namely HPH-2Trt, which induces apoptosis in human pancreatic adenocarcinoma AsPC-1 cells. Herein the influence of the imidazole substitution of HPH-2Trt was examined. Five related compounds, HPH-1Trt, HPH-2Bzl, HPH-1Bzl, HPH-2Me, and HPH-1Me were newly synthesized and screened for their activity against AsPC-1 and brain tumor cells U87 and U251. HPH-1Trt and HPH-2Trt were highly active among the tested HPH compounds. In vitro DNA cleavage assay showed both HPH-1Trt and HPH-2Trt completely disintegrate pUC19 DNA. The introduction of trityl group decisively potentiated the activity. (C) 2015 Elsevier Ltd. All rights reserved.