(8-thien-2-yloctyl)amine | 288323-65-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (8-thien-2-yloctyl)amine
• 英文别名: 8-(2-thienyl)octylamine；8-Thiophen-2-yloctan-1-amine
• CAS: 288323-65-9
• 化学式: C₁₂H₂₁NS
• 分子量: 211.371
• InChiKey: KSDJAQQGCJAGJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8-thien-2-yloctyl)amine 在 氢氧化钾 、 三氯化铝 、 萘 、 sodium 、 一水合肼 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 乙二醇 、 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 8-[5-(Piperidin-4-ylmethyl)thiophen-2-yl]octan-1-amine
  参考文献：
  名称：

  New polyamine-sensitive inhibitors of the NMDA receptor: Syntheses and pharmacological evaluation

  摘要：

  Derivatives of 5-(4-an-nobutyl)-2-thiophene-octylamine, a potent polyamine-sensitive inhibitor of the NMDA receptor, were synthesized and evaluated as inhibitors of [H-3]MK-801 binding to rat brain membranes. Alkylations of the terminal amino groups reduced inhibitory potency; only incorporation of the amino group of the short 4-aminobutyl arm into a piperidine ring was tolerated. Substitution of the thiophene nucleus with methyl or ethyl, and its replacement by a benzene nucleus, was of minor influence. The corresponding diguanidines exhibited high potency independent of chain length, whereas their sensitivity to spermine was sharply dependent on chain length. Insertion of an amide bond into the long octylamine arm increased sensitivity to spermine and to Tris buffer. Our results indicate that spermine sensitivity of [H-3]MK-801 binding inhibition is responsive to subtle changes in inhibitor structure and represents a promising target for pharmaceutical research. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.017
• 作为产物：
  描述：

  2-(8-phthalimidooctyl)thiophene 在 potassium chloride 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 (8-thien-2-yloctyl)amine
  参考文献：
  名称：

  Heterocyclic compounds for cancer chemoprevention

  摘要：

  一种包含杂环基团（如噻吩）与烷基异硫氰酸酯基团共价连接的化合物。该化合物可有效预防癌症或癌前病变的发生或进展，并可用于治疗或预防目的。该化合物可以制备并以药用组合物、化妆品、食品添加剂、补充剂等形式进行给药。本发明还提供了合成和使用该化学预防化合物的方法。

  公开号：

  US06166003A1

文献信息

• Design and Synthesis of D3R Bitopic Ligands with Flexible Secondary Binding Fragments: Radioligand Binding and Computational Chemistry Studies
  作者：Gui-Long Tian、Chia-Ju Hsieh、Michelle Taylor、Ji Youn Lee、Robert R. Luedtke、Robert H. Mach

  DOI：10.3390/molecules29010123

  日期：——

  A series of bitopic ligands based on Fallypride with a flexible secondary binding fragment (SBF) were prepared with the goal of preparing a D3R-selective compound. The effect of the flexible linker ((R,S)-trans-2a–d), SBFs ((R,S)-trans-2h–j), and the chirality of orthosteric binding fragments (OBFs) ((S,R)-trans-d, (S,R)-trans-i, (S,S)-trans-d, (S,S)-trans-i, (R,R)-trans-d, and (R,R)-trans-i) were evaluated in in vitro binding assays. Computational chemistry studies revealed that the interaction of the fragment binding to the SBF increased the distance between the pyrrolidine nitrogen and ASP1103.32 of the D3R, thereby reducing the D3R affinity to a suboptimal level.

  为了制备具有 D3R 选择性的化合物，我们制备了一系列基于具有柔性次级结合片段（SBF）的 Fallypride 位配体。在体外结合试验中评估了柔性连接体（(R,S)-反式-2a-d）、SBF（(R,S)-反式-2h-j）以及正交结合片段（OBF）（(S,R)-反式-d、(S,R)-反式-i、(S,S)-反式-d、(S,S)-反式-i、(R,R)-反式-d 和 (R,R)-反式-i）的手性的影响。计算化学研究显示，与 SBF 结合的片段的相互作用增加了吡咯烷氮与 D3R 的 ASP1103.32 之间的距离，从而将 D3R 亲和力降低到一个次优水平。
• US6166003A
  申请人：——

  公开号：US6166003A

  公开（公告）日：2000-12-26
• [EN] ISOTHIO CYANATO ALKYLTHIOPHENES AS CANCER CHEMOPROTECTIVE AGENTS<br/>[FR] ISOTHIO CYANATO ALKYLTHIOPHENES UTILISES COMME AGENTS CHIMIOPROTECTEURS CONTRE LE CANCER
  申请人：LKT LAB INC

  公开号：WO2000049013A1

  公开（公告）日：2000-08-24

  A compound comprising a heterocyclic moiety, such as a thiophene, covalently attached to an alkylene isothiocyanate moiety. The compound is effective to prevent the occurrence or progression of cancer or a precancerous condition, and can be used for therapeutic or prophylactic purposes. The compound can be provided and administered in the form of a pharmaceutical composition, a cosmetic, a food additive, supplement, or the like. Methods for synthesis and use of the chemopreventive compound of the invention are also provided.