3-(N-benzyliminomethyl)indole | 57506-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(N-benzyliminomethyl)indole
• 英文别名: N-benzyl-1-(1H-indol-3-yl)methanimine；3-(N-Benzylaminomethylen)-indol；benzyl-indol-3-ylmethylene-amine；N-[(E)-1H-indol-3-ylmethylidene]-1-phenylmethanamine
• CAS: 57506-52-2
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: WZIYTCPKLACXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(N-benzyliminomethyl)indole 在 吡啶 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 chiral P,N Trost's ligand 、 lithium carbonate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 35.0h， 生成 2-Benzyl-4-ethenyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic Alkylation

  摘要：

  A novel Pd-catalyzed intramolecular allylic alkylation of indoles allows THBCs and THGCs to be effectively synthesized in high yields and excellent enantiomeric excesses (ee up to 97%).

  DOI：

  10.1021/ja054109o
• 作为产物：
  描述：

  在 sodium nitrite 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(N-benzyliminomethyl)indole
  参考文献：
  名称：

  Synthesis and Evaluation of Schiff’s Base Indole Derivatives Against Inflammation Induced by Carrageenan in Rats

  摘要：

  Inflammation is a complex physiological response that can lead to various health issues. The development of effective anti-inflammatory agents is crucial for managing inflammatory conditions. This study focused on synthesizing and evaluating Schiff's base Indole derivatives for their anti-inflammatory potential. Among several synthesized compounds, C1IN, C2IN, C3IN, C7IN, C8IN, and C11IN demonstrated substantial reductions in paw edema and levels of cytokines of inflammation such as IL-1β and TNF-α. In-silico analysis and molecular docking studies further supported the observed effects, indicating potential interactions with TNF-α. The study highlights the therapeutic potential of Schiff's base Indole derivatives in mitigating inflammatory responses. Hence, Schiff's base Indole derivatives present a novel avenue for future research and the potential development of anti-inflammatory drugs.

  DOI：

  10.13005/ojc/400113

文献信息

• Antimykobakteriell wirksame Indolderivate
  作者：Siavosh Mahboobi、Götz Grothus、Wolfgang Meindl

  DOI：10.1002/ardp.19943270209

  日期：——

  yl)‐propanen 3. ‐ Umsetzungen der Aldehyde 4 bzw. 10 mit den Benzylaminen 12 sowie der Indolylalkylamine 6a bzw. 9a mit den Benzaldehyden 11 und Reduktionen der Schiffbasen führen zu N‐Benzyl‐(indol‐3‐ylmethyl)‐aminen 13 und N‐Benzyl‐(indol‐3‐ylethyl)‐aminen 14. ‐ Die tert Amine 16 werden über die Formamide 15, Amine 18 nach Mannich synthetisiert. ‐ Alle Verbindungen werden auf wachstumshemmende Wirkung

  硝基甲烷与吲哚基硝基乙烯 2 的迈克尔加成生成 1,3-二硝基-2-（吲哚-3'-基）-丙烷 3. - 醛 4 和 10 与苄胺 12 和吲哚烷基胺 6a 和 9a 与苯甲醛 11 和席夫碱的还原导致 N-苄基-（吲哚-3-基甲基）-胺 13 和 N-苄基-（吲哚-3-基乙基）-胺 14。 - 叔胺 16 通过甲酰胺形成15，根据Mannich合成的胺18。- 检查所有化合物对结核分枝杆菌 H 37 Ra 的生长抑制作用。根据结构讨论抗真菌活性。
• Sequential One-Pot Cyclizations: Concise Access to the ABCE Tetracyclic Framework of <i>Strychnos</i> Alkaloids
  作者：Gopal Sirasani、Rodrigo B. Andrade

  DOI：10.1021/ol9004799

  日期：2009.5.21

  A sequential one-pot biscyclization route to the ABCE tetracyclic framework of Strychnos alkaloids has been developed. Specifically, the AgOTf-mediated spirocyclization of an appropriately functionalized indole 3-carbinamide afforded a stable spiroindolenine intermediate; subsequent addition of DBU to the reaction mixture effected an unprecedented intramolecular aza-Baylis−Hillman reaction, delivering

  到的ABCE四环框架的一个连续一锅biscyclization路线马钱子生物碱已经研制成功。具体地，通过AgOTf介导的适当官能化的吲哚3-碳酰胺的螺环化提供了稳定的螺环吲哚中间体。随后向反应混合物中添加DBU进行了前所未有的分子内aza-Baylis-Hillman反应，以70％的分离产率提供了四环产物。
• Streptochlorin analogues as potential antifungal agents: Design, synthesis, antifungal activity and molecular docking study
  作者：Ya Gao、Dai-Chuan Huang、Chang Liu、Zi-Long Song、Jing-Rui Liu、Shu-Ke Guo、Jun-Yang Tan、Run-Ling Qiu、Bing Jin、Haifeng Zhang、Nick Mulholland、Xinya Han、Qinfei Xia、Abdallah S. Ali、Dale Guo、Yun Deng、Yu-Cheng Gu、Ming-Zhi Zhang

  DOI：10.1016/j.bmc.2021.116073

  日期：2021.4

  improve its antifungal activity. Our work in this paper focused on the replacement of oxazole ring in streptochlorin with the imidazole ring, to discover novel analogues. Based on this design strategy, three series of streptochlorin analogues were efficiently synthesized through sequential Vilsmeier-Haack reaction, Van Leusen imidazole synthesis and halogenation reaction. Some of the analogues displayed

  链绿素是一种从海洋链霉菌属中分离的吲哚生物碱小分子，在我们之前的研究中，由于其在预防许多植物病原体方面具有强大的生物活性，因此它是一种很有前途的先导化合物，但需要进一步的结构修饰以提高其抗真菌活性。我们在本文中的工作重点是用咪唑环取代链绿素中的恶唑环，以发现新的类似物。基于此设计策略，通过连续的 Vilsmeier-Haack 反应、Van Leusen 咪唑合成和卤化反应，高效合成了三个系列的链绿素类似物。一些类似物在初步分析中显示出优异的活性，化合物4g和4i突出显示了这一点, 50 μg/mL 下对链格孢属叶斑病和立枯病菌的生长抑制率分别为 97.5% 和 90.3%，甚至比链绿素、pimprinine 和 Osthole 更有效。分子对接模型表明，链绿素与嗜热菌Leucyl-tRNA 合成酶的结合方式与AN2690 相似，为链绿素衍生物抗真菌活性的作用模式研究提供了一个视角。进一步
• Allosteric Functional Switch of Neurokinin A-Mediated Signaling at the Neurokinin NK2 Receptor: Structural Exploration
  作者：Céline Valant、Emeline Maillet、Jean-Jacques Bourguignon、Bernard Bucher、Valérie Utard、Jean-Luc Galzi、Marcel Hibert

  DOI：10.1021/jm900671k

  日期：2009.10.8

  The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: resting-inactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while CAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator.
• Kumar, P.; Nath, C.; Bhargava, K.P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 1128 - 1129
  作者：Kumar, P.、Nath, C.、Bhargava, K.P.、Shanker, K.

  DOI：——

  日期：——