2-(benzofuran-2-yl)ethyl 4-methylbenzenesulfonate

• 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: 2-(benzofuran-2-yl)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-(benzofuran-2-yl)ethyl tosylate；2-(1-Benzofuran-2-yl)ethyl 4-methylbenzenesulfonate
• 化学式: C₁₇H₁₆O₄S
• 分子量: 316.378
• InChiKey: UVDCEJJTNFWPSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzofuran-2-yl)ethyl 4-methylbenzenesulfonate 、 1-(4-氯苯基)哌嗪 在 三乙胺 作用下， 以 乙腈 为溶剂， 以93%的产率得到1-(2-(benzofuran-2-yl)ethyl)-4-(4-chlorophenyl)piperazine
  参考文献：
  名称：

  Identification of a new selective dopamine D4 receptor ligand

  摘要：

  The dopamine D-4 receptor has been shown to play key roles in certain CNS pathologies including addiction to cigarette smoking. Thus, selective D-4 ligands may be useful in treating some of these conditions. Previous studies in our laboratory have indicated that the piperazine analog of haloperidol exhibits selective and increased affinity to the DAD(4) receptor subtype, in comparison to its piperidine analog. This led to further exploration of the piperazine moiety to identify new agents that are selective at the D-4 receptor. Compound 27 (KiD4 = 0.84 nM) was the most potent of the compounds tested. However, it only had moderate selectivity for the D-4 receptor. Compound 28 (KiD4 = 3.9 nM) while not as potent, was more discriminatory for the D-4 receptor subtype. In fact, compound 28 has little or no binding affinity to any of the other four DA receptor subtypes. In addition, of the 23 CNS receptors evaluated, only two, 5HT(1A)R and 5HT(2B)R, have binding affinity constants better than 100 nM (K-i < 100 nM). Compound 28 is a potentially useful D-4-selective ligand for probing disease treatments involving the D-4 receptor, such as assisting smoking cessation, reversing cognitive deficits in schizophrenia and treating erectile dysfunction. Thus, further optimization, functional characterization and evaluation in animal models may be warranted. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.04.026
• 作为产物：
  描述：

  2-碘苯酚 在 4-二甲氨基吡啶 、 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 2-(benzofuran-2-yl)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  靶向SSRI / 5-HT 1A / 5-HT 7的新型芳烷基哌嗪衍生物的合成及类抗抑郁活性

  摘要：

  合成了一系列新型的芳烷基哌嗪衍生物，并对其5-羟色胺再摄取抑制和5-HT 1A / 5-HT 7受体亲和力活性进行了评估。使用强制游泳试验（FST）和尾部悬浮试验（TST）筛选了化合物的体内抗抑郁活性。结果表明化合物21k（RUI，IC 50  = 31 nM; 5-HT 1A，5-HT 7，k i  = 62，12 nM）和21n（RUI，IC 50  = 25 nM; 5-HT 1A，5 -HT 7，K我 = 28，3.3纳米）表现出高的亲和性对5-HT 1A/ 5-HT 7受体结合有效的5-羟色胺再摄取抑制作用。具体而言，最有前途的化合物21n具有良好的口服药代动力学特性和可接受的hERG谱，并且在FST和TST模型中显示出有效的抗抑郁样作用。

  DOI：

  10.1016/j.ejmech.2017.12.063

文献信息

• Synthesis of iboga-like isoquinuclidines: Dual opioid receptors agonists having antinociceptive properties
  作者：Tuhin Suvro Banerjee、Sibasish Paul、Surajit Sinha、Sumantra Das

  DOI：10.1016/j.bmc.2014.09.001

  日期：2014.11

  and (CH2)3 linkers have been synthesized with the view to develop potential antinociceptive drugs. The compounds 14 and 21 showed binding at the μ-opioid receptor (MOR), while the compound 11a exhibited dual affinities at both MOR and κ-opioid receptor (KOR). MAP kinase activation indicated all three compounds have opioid agonistic properties. The presence of a double bond and endo-methylcarboxylate

  为了开发潜在的抗伤害性药物，已经合成了一些新颖的伊博加类似物，这些类似物由苯并呋喃部分和通过–CH 2 –，（CH 2）2和（CH 2）3连接子连接的脱氢异喹啉环组成。化合物14和21在μ阿片受体（MOR）处显示出结合，而化合物11a在MOR和κ阿片受体（KOR）处均显示出双重亲和力。MAP激酶激活表明所有三种化合物均具有阿片样物质的激动特性。双键和内键的存在脱氢异喹啉环上的-甲基羧酸酯基团和苯并呋喃和亚甲基间隔基似乎是阿片受体结合必不可少的。进一步的研究表明，在热板试验中11a引起了小鼠明显的镇痛作用，与吗啡产生的镇痛作用相当。与各种伊博加同源物不同，化合物11a也被发现是非致畸性的。这项研究确定了一种新的药效基团，可导致开发适用的吗啡替代品来治疗疼痛。
• Synthesis of new series of iboga analogues
  作者：Sibasish Paul、Sankha Pattanayak、Surajit Sinha

  DOI：10.1016/j.tetlet.2011.09.040

  日期：2011.11

  Synthesis of new iboga-analogues, replacing the indole ring with a benzofuran moiety has been described. Starting materials are the suitably substituted benzofuran derivatives and have been synthesized by Pd-catalyzed reactions. The conversion of endo-6-methylcarboxylate substituted dehydroisoquinuclidine to exo-isomer, a key component of iboga-alkaloids has been achieved in the presence of NaOMe in

  已经描述了新的伊博加类似物的合成，其用苯并呋喃部分取代了吲哚环。起始原料是适当取代的苯并呋喃衍生物，并已通过Pd催化反应合成。的转化率内-6-甲基羧酸取代dehydroisoquinuclidine到外型-异构体，iboga生物碱的一个关键组成部分已经在NaOMe的甲醇的存在下在回流条件下实现的。
• Benzofuran derivatives and pharmaceutical compositions containing the same
  申请人：——

  公开号：US20040053940A1

  公开（公告）日：2004-03-18

  Benzofuran derivatives represented by formula (I) or salts thereof: 1 (wherein R 1 represents a phenyl group or a hydrogen atom; k is 0 or 1; each of m, n, o, p, and q is an integer of 0 to 5; and each of R 2 and R 3 represents a hydrogen atom or a hydroxyl group, or R 2 and R 3 together represent an oxygen atom, with proviso that k, q, and m, or n, o, and p are not simultaneously 0). The compounds inhibit phosphorylation of STAT 6 and are useful in the treatment or prevention of allergic diseases.

  式(I)所表示的苯并呋喃衍生物或其盐：1（其中R1表示苯基或氢原子；k为0或1；m、n、o、p和q中的每一个是0至5的整数；R2和R3中的每一个表示氢原子或羟基，或R2和R3一起表示氧原子，但k、q和m，或n、o和p不能同时为0）。这些化合物可以抑制STAT 6的磷酸化，并可用于治疗或预防过敏性疾病。
• BENZOFURAN DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：POLA CHEMICAL INDUSTRIES, INC.

  公开号：EP1346987B1

  公开（公告）日：2006-05-03
• US4129655A
  申请人：——

  公开号：US4129655A

  公开（公告）日：1978-12-12