N-(3-氟苄基)乙烷-1,2-二胺 | 123566-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-氟苄基)乙烷-1,2-二胺
• 英文名称: N-(3-fluorobenzyl)ethylenediamine
• 英文别名: N-(3-Fluorobenzyl)ethane-1,2-diamine；N'-[(3-fluorophenyl)methyl]ethane-1,2-diamine
• CAS: 123566-39-2
• 化学式: C₉H₁₃FN₂
• mdl: MFCD04360486
• 分子量: 168.214
• InChiKey: OPQMQZYIHOTTEL-UHFFFAOYSA-N

物化性质

• 沸点：
  89-91 °C(Press: 0.007 Torr)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 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：
  38
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(3-氟苄基)乙烷-1,2-二胺 在 N-甲基吡咯烷酮 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 生成 1-(3-fluorobenzyl)imidazoline-2-thione
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051
• 作为产物：
  描述：

  乙二胺 、 3-氟苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以68%的产率得到N-(3-氟苄基)乙烷-1,2-二胺
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051

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。
• Design, Synthesis, and Synergistic Activities of Eight‐Membered Carbon Bridged Neonicotinoid Derivatives
  作者：Du Tan、Xiaoyong Xu、Zhong Li、Zhiping Xu、Xusheng Shao

  DOI：10.1002/cbdv.202301412

  日期：2024.2

  Insecticide synergists are an effective approach to increase the control efficacy and reduce active ingredient usage. In order to explore neonicotinoid-specific synergists with novel scaffolds and higher potency, a series of eight-membered carbon bridged neonicotinoid derivatives were designed and synthesized in accordance with our previous research. The synergistic effects of the target compounds

  杀虫增效剂是提高防治效果和减少活性成分使用量的有效方法。为了探索具有新颖支架和更高效力的新烟碱类特异性增效剂，根据我们前期的研究，设计并合成了一系列八元碳桥新烟碱类衍生物。评价了目标化合物对蚜虫新烟碱类杀虫剂的协同作用，并总结了构效关系。结果表明，大多数目标化合物在低浓度下对羊螈中的吡虫啉表现出显着的协同作用。特别地，浓度为1mg/L的化合物1将吡虫啉的LC 50值从0.856mg/L降低至0.170mg/L。同时，化合物1还提高了属于杀虫剂抗性行动委员会 (IRAC) 4 A 亚组的大多数新烟碱类杀虫剂对A. craccivora 的杀虫活性。本研究对于指导新烟碱类特异性增效剂的设计可能有意义。
• Substituted 1-aralkyl imidazoline-2-thiols
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0329900A1

  公开（公告）日：1989-08-30

  Compounds of structure (I) and pharmaceutically acceptable salts thereof are described in which, n is 0 to 5; X¹ to X⁵ are any accessible combination of hydrogen, halogen, C₁₋₆alkyl, C₁₋₄alkoxy, cyano, nitro, SONH₂, SO₂CH₃, SO₂CH₂F, SO₂CHF₂, SO₂CF₃, CF₃, CHO, OH, (CH₂)OH, CO₂H, or CO₂CpH2p+1wherein p is 1 to 4; R is hydrogen, C₁₋₄alkyl or (CH₂)m-CO₂R¹; m is 0 to 5; and R¹ is H or C₁₋₄alkyl. These compounds are dopamine-β-hydroxylase inhibitors. Pharmaceutical compositions are described as are methods of use. Processes for the preparation of these compounds are described.

  结构(I)的化合物 及其药学上可接受的盐类，其中，n 为 0 至 5；X¹ 至 X⁵ 是氢、卤素、C₁₋₆烷基、C₁₋₄烷氧基、氰基、硝基、SONH₂、SO₂CH₃、SO₂CH₂F、SO₂CHF₂、SO₂CF₃、CF₃、CHO、OH、(CH₂)OH、CO₂H 或 CO₂CpH2p+1，其中 p 为 1 至 4；R 是氢、C₁₋₄烷基或 (CH₂)m-CO₂R¹；m 是 0 至 5；R¹ 是 H 或 C₁₋₄ 烷基。 这些化合物是多巴胺-β-羟化酶抑制剂。药剂组合物和使用方法均有描述。还描述了制备这些化合物的工艺。
• 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.
• Quinazolindione derivatives as potent 5-HT3A receptor antagonists
  作者：Byung-Hwan Lee、Min Jung Choi、Mi Na Jo、Hee Jeong Seo、Seung-Yeol Nah、Yong Seo Cho、Ghilsoo Nam、Ae Nim Pae、Hyewhon Rhim、Hyunah Choo

  DOI：10.1016/j.bmc.2009.04.029

  日期：2009.7

  5-HT3A receptor antagonists have been used mainly for the treatment of nausea and vomiting. These days, the antagonists are of special interest due to their therapeutic potential to treat other diseases such as depression, psychotic disorder, drug abuse, and irritable bowel syndrome. To discover novel 5-HT3A receptor antagonists, we screened our in-house small molecule library, resulting in identifying the quinazolindione derivatives as potent 5-HT3A receptor antagonists. For the purpose of structure-activity relationship study, 24 quinazolindione analogues were biologically evaluated against 5-HT3A receptor. Among those, KKHT10612 shows the best antagonistic effect against 5-HT3A receptor with an IC50 value of 0.8 mu M which is comparable with that of the reference compound, MDL72222, and selectivity over T-type calcium channel as well. (C) 2009 Elsevier Ltd. All rights reserved.