ethyl 3-iodo-1-phenylsulfonyl-2-indolecarboxylate | 153827-71-5

• 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: ethyl 3-iodo-1-phenylsulfonyl-2-indolecarboxylate
• 英文别名: ethyl-1-benzenesulfonyl-3-iodo-1H-indole-2-carboxylate；Ethyl 3-iodo-1-phenylsulfonylindole-2-carboxylate；ethyl 3-iodo-1-(phenylsulfonyl)-1H-indole-2-carboxylate；ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate；ethyl 1-benzenesulfonyl-3-iodoindole-2-carboxylate；1H-Indole-2-carboxylic acid, 3-iodo-1-(phenylsulfonyl)-, ethyl ester；ethyl 1-(benzenesulfonyl)-3-iodoindole-2-carboxylate
• CAS: 153827-71-5
• 化学式: C₁₇H₁₄INO₄S
• 分子量: 455.273
• InChiKey: XGZMLOLDNRXPKC-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  563.0±53.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-iodo-1-phenylsulfonyl-2-indolecarboxylate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 cesium fluoride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 3-苯基-1H-吲哚-2-羧酸
  参考文献：
  名称：

  Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists

  摘要：

  We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl) methyl]1-(1-naphthyl) ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.019
• 作为产物：
  描述：

  3-碘-1H-吲哚-2-甲酸乙酯 、 苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 16.75h， 以85%的产率得到ethyl 3-iodo-1-phenylsulfonyl-2-indolecarboxylate
  参考文献：
  名称：

  应用基于异氰化物的多组分反应合成吲哚苯并氮杂酮

  摘要：

  Ugi 多组分反应对含氧酸 4 的应用允许以高达 72 % 的良好产率形成潜在的 5 型抗有丝分裂吲哚苯并氮杂酮，而从起始底物 6 的相同转化可以以高达 89 的产率获得 paullone 的类似物%。该反应可应用于多种异氰化物，从而确保在关键的 C-5 位置引入分子多样性。环己烯基异氰化物的使用允许缩合后改性，而仔细选择胺和吲哚保护基团被证明对于提供生物测试所需的脱保护化合物很重要。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200800643

文献信息

• Preparation and palladium-catalysed arylation of indolylzinc halides
  作者：Takao Sakamoto、Yoshinori Kondo、Nobuo Takazawa、Hiroshi Yamanaka

  DOI：10.1039/p19960001927

  日期：——

  Indolylzinc halides are prepared by two methods: transmetallation of indolyllithiums with zinc chloride and oxidative addition of active zinc to iodoindoles. The palladium-catalysed reaction of the indolylzinc halides provides a practical method for synthesizing arylindoles.

  吲哚锌卤化物通过两种方法制备：吲哚锂与氯化锌的金属转移反应，以及活性锌对碘代吲哚的氧化加成反应。钯催化的吲哚锌卤化物反应为合成芳基吲哚提供了一种实用方法。
• Synthesis of β-Carbolines from 2-Acyl-1-benzenesulfonyl-3-iodo-1<b><i>H</i></b>-indoles
  作者：Elisabetta Rossi、Giorgio Abbiati、Egle Beccalli、Alessandro Marchesini

  DOI：10.1055/s-2001-18715

  日期：——

  2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles and 1-benzenesulfonyl-3-iodo-1H-indole-2-carbaldehyde give in satisfactory yields 1,3- and 3-substituted-β-carbolines, respectively, by combined palladium-catalyzed coupling with alk-1-ynes followed by 6-endo-dig cycloamination reactions.

  2-酰基-1-苯磺酰基-3-碘-1H-吲哚和1-苯磺酰基-3-碘-1H-吲哚-2-羧醛通过与 alk-1-炔的联合钯催化耦合反应，随后进行6-端内环的环氨化反应，以令人满意的产率分别生成1,3-和3-取代的β-吲哚啉。
• New C5-Alkylated Indolobenzazepinones Acting as Inhibitors of Tubulin Polymerization: Cytotoxic and Antitumor Activities
  作者：Laurent Keller、Stéphane Beaumont、Jian-Miao Liu、Sylviane Thoret、Jérôme S. Bignon、Joanna Wdzieczak-Bakala、Philippe Dauban、Robert H. Dodd

  DOI：10.1021/jm701466p

  日期：2008.6.1

  A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate alpha-alkylbenzylamino o-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 mu M. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.
• Indolylzinc iodides by oxidative addition of active zinc to iodoindoles
  作者：Takao Sakamoto、Yoshinori Kondo、Nobuo Takazawa、Hiroshi Yamanaka

  DOI：10.1016/s0040-4039(00)73824-x

  日期：1993.9

  Indolylzinc derivatives were prepared by the oxidative addition of active zinc to iodoindoles, which coupled with aromatic halides in the presence of palladium catalyst to give arylated indoles.
• Rigid Analogues of Antimitotic Indolobenzazepinones: New Insights into Tubulin Binding via Molecular Modeling
  作者：Valérie Pons、Stéphane Beaumont、Marie Elise Tran Huu Dau、Bogdan I. Iorga、Robert H. Dodd

  DOI：10.1021/ml200024y

  日期：2011.8.11

  Two rigid analogues of 5-ethylindolobenzazepinone 4, a potent c-ytotoxic agent and inhibitor of tubulin polymerization, were prepared. The first was the indane derivative 5, in which the ethyl group is attached to the benzo moiety. The second was the pyrrolidine analogue 6, in which the ethyl chain was bound to the lactam nitrogen. While both compounds were considerably less active inhibitors of KB cell growth as compared to 4, inhibition of tubulin polymerization was only moderately reduced. Tubulin docking studies indicated that the aR and aS atropoisomers of 5 and 6 occupy different binding pockets at the colchicine binding site. Conversely, both aS-5 and aS-6 occupy the same binding pocket as aSS-4 but do not benefit from the favorable hydrophobic interactions provided by the CS alkyl group of 4, thus possibly explaining their lower activities.