N-(p-nitrobenzyl)ethylenediamine | 102494-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(p-nitrobenzyl)ethylenediamine
• 英文别名: N-(4-nitro-benzyl)-ethylenediamine；N-(4-Nitro-benzyl)-aethylendiamin；N'-[(4-nitrophenyl)methyl]ethane-1,2-diamine
• CAS: 102494-88-2
• 化学式: C₉H₁₃N₃O₂
• 分子量: 195.221
• InChiKey: GTABIVQKUMXCSY-UHFFFAOYSA-N

物化性质

• 沸点：
  360.1±22.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(p-nitrobenzyl)ethylenediamine 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 117.0h， 生成 N,N,N'-tris[(6-carboxy-2,2'-bipyridine-5'-yl)methyl]-N'-p-nitrobenzylethylenediamine
  参考文献：
  名称：

  带有 5'-取代-6-羧基-2,2'-联吡啶亚基的柔性多齿配体的合成

  摘要：

  研究了不对称5',6-二取代-2,2'-联吡啶在制备柔性多主题配体中的合成范围。关键的 6-bromo-5'-bromomethyl-2,2'-bipyridine 结构单元的制备涉及 Krohnke 方案，然后是经过优化的自由基溴化反应。6-bromo-5'-bromomethyl-2,2'-bipyridine 的功能化已经通过 Delepine 和 Gabriel 反应实现，水解后提供相应的氨基化合物，而醋酸盐的亲核攻击随后皂化反应提供相应的酒精。多官能化联吡啶配体已通过碱辅助亲核取代从 6-bromo-5'-bromomethyl-2,2'-bipyridine 和无环胺或伯醇一步制备。在所有情况下，在温和的条件下，使用钯促进的乙氧基化反应使溴官能团转化为相应的乙酯成为可能，而碱性条件下的皂化在质子化后提供相应的酸。本文报道的协议的效用已扩展到乙二胺平台的合成，该平台带有附加的 4-硝基苄基，用于潜在地连接到其他分子。

  DOI：

  10.1055/s-2002-31968
• 作为产物：
  描述：

  乙二胺 、 对硝基溴化苄 以 二氯甲烷 为溶剂， 反应 5.0h， 以96%的产率得到N-(p-nitrobenzyl)ethylenediamine
  参考文献：
  名称：

  带有 5'-取代-6-羧基-2,2'-联吡啶亚基的柔性多齿配体的合成

  摘要：

  研究了不对称5',6-二取代-2,2'-联吡啶在制备柔性多主题配体中的合成范围。关键的 6-bromo-5'-bromomethyl-2,2'-bipyridine 结构单元的制备涉及 Krohnke 方案，然后是经过优化的自由基溴化反应。6-bromo-5'-bromomethyl-2,2'-bipyridine 的功能化已经通过 Delepine 和 Gabriel 反应实现，水解后提供相应的氨基化合物，而醋酸盐的亲核攻击随后皂化反应提供相应的酒精。多官能化联吡啶配体已通过碱辅助亲核取代从 6-bromo-5'-bromomethyl-2,2'-bipyridine 和无环胺或伯醇一步制备。在所有情况下，在温和的条件下，使用钯促进的乙氧基化反应使溴官能团转化为相应的乙酯成为可能，而碱性条件下的皂化在质子化后提供相应的酸。本文报道的协议的效用已扩展到乙二胺平台的合成，该平台带有附加的 4-硝基苄基，用于潜在地连接到其他分子。

  DOI：

  10.1055/s-2002-31968

文献信息

• Design, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues
  作者：Xiao Zhang、Yiping Wang、Zhiping Xu、Xusheng Shao、Zewen Liu、Xiaoyong Xu、Peter Maienfisch、Zhong Li

  DOI：10.1021/acs.jafc.0c04786

  日期：2021.3.17

  cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogues of IPPA08 by converting the pyridyl moiety of IPPA08 into phenyl groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found

  由于杀虫剂增效剂具有通过减少剂量的活性成分来提高杀虫剂控制功效的潜力，因此受到人们的追捧。我们先前曾报道，顺式构型的新烟碱类（IPPA08）对新烟碱类杀虫剂表现出特定的协同活性。在这项研究中，我们通过硝基亚甲基化合物与戊二醛之间的便捷双曼尼希缩合反应，将IPPA08的吡啶基部分转化为苯基，从而合成了IPPA08的一系列结构类似物。发现所有的羰桥新烟碱类化合物均可增强吡虫啉对蚜虫的毒性。值得注意的是，浓度为0.75 mg / L的化合物25降低了吡虫啉对Cr。craccivora的LC 50值IPPA08的LC 50值降低了6.54倍，而LC 50值降低了3.50倍。蜂毒性试验的结果表明，化合物25关于对蜜蜂吡虫啉毒性（在它的影响显示选择性蜜蜂L.）。总之，用苯环取代吡啶环是获得新烟碱类杀虫剂具有氧桥缩合部分的新型增效剂的可行方法。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Triazole Compounds and Methods of Making and Using the Same
  申请人：Rib-X Pharmaceuticals, Inc.

  公开号：US20140094422A1

  公开（公告）日：2014-04-03

  The present invention provides triazole macrocyclic compounds useful as therapeutic agents. More particularly, these compounds are useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. These compounds are represented by the following formula (I): wherein R 1 , R 2 , etc. are defined as in Claim 1.

  本发明提供了三唑大环化合物，可用作治疗剂。更具体地说，这些化合物可用作抗感染、抗增殖、抗炎和促动力剂。这些化合物由以下式（I）表示：其中，R1，R2等如权利要求书1中所定义。
• Process for preparing isothiocyanato functionalized metal complexes
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0374947A1

  公开（公告）日：1990-06-27

  The present invention is directed to a novel process for preparing isothiocyanate fuctionalized chelates by reacting amino fuctionalized chelates with thiophosgene.

  本发明涉及一种新工艺，通过使氨基螯合物与硫代磷酰氯反应制备异硫氰酸酯化螯合物。
• Binding activity of substituted benzyl derivatives of chloronicotinyl insecticides to housefly-head membranes, and its relationship to insecticidal activity against the houseflyMusca domestica
  作者：Hisashi Nishiwaki、Yoshiaki Nakagawa、David Y Takeda、Atsushi Okazawa、Miki Akamatsu、Hisashi Miyagawa、Tamio Ueno、Keiichiro Nishimura

  DOI：10.1002/1526-4998(200010)56:10<875::aid-ps220>3.0.co;2-a

  日期：2000.10

  Variously substituted benzyl derivatives of chloronicotinyl insecticides were synthesized with a wide range of substituents including halogens, NO2, CN, CF, and small alkyl and alkoxy groups at the ortho, meta and para positions, as well as multiple-substituted benzyl analogues. Their binding activity to the alpha-bungarotoxin binding site in housefly (Musca domestica) head membrane preparations was measured. Among the compounds tested, the activity of the meta-CN derivative was the highest, being 20-100 times higher than those of imidacloprid, acetamiprid and nitenpyram. The synergized insecticidal activity against houseflies was also measured for selected compounds with the metabolic inhibitor, NIA16388 (propargyl propyl phenylphosphonate). For the nitromethylene analogues, including both benzyl and pyridylmethyl analogues, higher binding activity usually resulted in higher insecticidal activity. (C) 2000 Society of Chemical Industry.