1-((2,4,6-triisopropylphenyl)sulfonyl)-1H-indole | 70390-92-0

• 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: 1-((2,4,6-triisopropylphenyl)sulfonyl)-1H-indole
• 英文别名: 1-(2,4,6-Triisopropyl-benzenesulfonyl)-1H-indole；1-[2,4,6-tri(propan-2-yl)phenyl]sulfonylindole
• CAS: 70390-92-0
• 化学式: C₂₃H₂₉NO₂S
• 分子量: 383.555
• InChiKey: DHNVTONAMJRUMO-UHFFFAOYSA-N

物化性质

• 沸点：
  501.0±60.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((2,4,6-triisopropylphenyl)sulfonyl)-1H-indole 在 硝酸 、 乙酸酐 作用下， 以 水 为溶剂， 以55%的产率得到N-((2,4,6-triisopropylphenyl)sulfonyl)-3-nitroindole
  参考文献：
  名称：

  钯（0）催化的3-硝基吲哚与乙烯基环丙烷的脱芳香族化合物[3 + 2]环加成反应：立体定义的2,3-熔融环戊鞣二氢吲哚衍生物

  摘要：

  描述了钯（0）催化的3-硝基吲哚与乙烯基环丙烷的非对映选择性脱芳香环戊烯环化反应。这种直接且高度原子经济的方法导致了多种官能化的二氢吲哚，具有良好的收率和非对映选择性，代表了有价值的2,3-稠合环戊环二氢吲哚骨架的空前进入。

  DOI：

  10.1021/acs.orglett.7b00784
• 作为产物：
  描述：

  吲哚 、 2,4,6-三异丙基苯磺酰氯 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以86%的产率得到1-((2,4,6-triisopropylphenyl)sulfonyl)-1H-indole
  参考文献：
  名称：

  通过Rh迁移策略立体选择性合成乙烯基环丙[b]吲哚。

  摘要：

  已开发出一种温和的铑催化体系，通过将吲哚与原位环丙烯开环生成的乙烯基类胡萝卜素进行环丙烷化，来合成乙烯基环丙烷[ b ]二氢吲哚。通过采用Rh迁移策略，可以获得具有良好或优异的E：Z比（≤99：1）和完全非对映选择性（≤99：1）的产物。该方法容易，催化剂负载低并且适用于广泛的功能。

  DOI：

  10.1021/acs.orglett.0c02071

文献信息

• Palladium(0)-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined 2,3-Fused Cyclopentannulated Indoline Derivatives
  作者：Maxime Laugeois、Johanne Ling、Charlène Férard、Véronique Michelet、Virginie Ratovelomanana-Vidal、Maxime R. Vitale

  DOI：10.1021/acs.orglett.7b00784

  日期：2017.5.5

  The palladium(0)-catalyzed diastereoselective dearomative cyclopentannulation of 3-nitroindoles with vinylcyclopropanes is described. This straightforward and highly atom-economical method leads to a wide range of functionalized indolines in good yields and diastereoselectivities and represents an unprecedented entry toward the valuable 2,3-fused cyclopentannulated indoline scaffold.

  描述了钯（0）催化的3-硝基吲哚与乙烯基环丙烷的非对映选择性脱芳香环戊烯环化反应。这种直接且高度原子经济的方法导致了多种官能化的二氢吲哚，具有良好的收率和非对映选择性，代表了有价值的2,3-稠合环戊环二氢吲哚骨架的空前进入。
• 1,2-Bis(phenylsulfonyl)indole as an acceptor of organocuprate nucleophiles
  作者：Gordon Wayne Gribble、David C Qian、Philip E Alford、Tara L S Kishbaugh、Sean T Jones

  DOI：10.3998/ark.5550190.0011.406

  日期：——

  Bis(phenylsulfonyl)-1H-indole is a novel example of an electron-deficient indole that undergoes nucleophilic attack at C-3. Though a variety of other organometallic nucleophiles fail to engender nucleophilic substitution, organocuprates produce 3-substituted 2-(phenylsulfonyl)- 1H-indoles. These reactions contribute to the growing number of examples of nucleophilic addition to the indole core.

  双（苯基磺酰基）-1H-吲哚是缺电子吲哚的一个新例子，它在 C-3 处发生亲核攻击。尽管各种其他有机金属亲核试剂无法产生亲核取代，但有机铜酸盐会产生 3-取代的 2-（苯磺酰基）- 1H-吲哚。这些反应导致吲哚核亲核加成的例子越来越多。
• 一种烯基环丙烷吲哚啉化合物及其制备方法
  申请人：南京工业大学

  公开号：CN111777545A

  公开（公告）日：2020-10-16

  本发明公开了一种烯基环丙烷吲哚啉化合物及其制备方法，本发明通过将化合物A、化合物B和Rh2(esp)2混合，然后加入溶剂二氯甲烷，得到反应液，于20～40℃下搅拌至反应结束，在反应结束后过滤除去反应液中的不溶性固体，将所得溶液减压浓缩除去溶剂后，再通过柱色谱法纯化，得到目标产物烯基环丙烷吲哚啉化合物；其中，所述化合物A为携带R1基团的2,4,6‑三异丙基苯磺酰基吲哚；化合物B为1号位为R2和R3基团的环丙烯。本发明制备方法所需工艺条件简单，反应条件温和，能够有效得到高选择性的烯基环丙烷吲哚啉化合物，反应有较好的底物适用性及原子经济性；本发明所合成的烯基环丙烷吲哚啉化合物是制备其他天然产物的有用的合成中间体。
• 4-(1-(sulfonyl)-1h-indol-2-yl)-4-(hydroxy)-cyclohexa-2,5-dienone compounds and analogs thereof as therapeutic agents
  申请人：Stevens Francis Graham Malcolm

  公开号：US20060100265A1

  公开（公告）日：2006-05-11

  This invention pertains to certain 4-(1-(sulfonyl)-1H-indol-2-yl)-4-(hydroxy)-cyclohexa-2,5-dienone compounds, and analogs thereof, including compounds of the following formula, which are, inter alia, antiproliferative agents, anticancer agents, and/or thioredoxin/thioredoxin reductase inhibitors: formula (I) wherein: Ar is a 1-(sulfonyl)-1H-indol-2-yl group; the bond marked α is independently: (a) a single bond; or: (b) a double bond; the bond marked β is independently: (a) a single bond; or: (b) a double bond; the group —OR O is independently: (a) —OH; (b) an ether group (e.g., —OMe); or: (c) an acyloxy (i.e., reverse ester) group (e.g., —OC(═O)Me); each of R 2 , R 3 , R 5 , and R 6 , is independently a ring substituent and is: (a) H; (b) a monovalent monodentate substituent; or: (c) a ring substituent which, together with an adjacent ring substituent, and together with the ring atoms to which these ring substituents are attached, form a fused ring; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for example, in the treatment of proliferative conditions, (e.g., cancer), and/or conditions mediated by thioredoxin/thioredoxin reductase.

  本发明涉及某些4-(1-(磺酰基)-1H-吲哚-2-基)-4-(羟基)-环己-2,5-二酮化合物及其类似物，包括以下式的化合物，它们是抗增殖剂、抗癌剂和/或硫代还蛋白/硫代还蛋白还原酶抑制剂等：式(I)其中：Ar是1-(磺酰基)-1H-吲哚-2-基；标记为α的键独立地是：(a) 单键；或：(b) 双键；标记为β的键独立地是：(a) 单键；或：(b) 双键；—ORO基团独立地是：(a) -OH；(b) 醚基团（例如，-OMe）；或：(c) 酰氧基（即反酯基）基团（例如，-OC（═O）Me）；R2、R3、R5和R6中的每一个独立地是一个环取代基，并且是：(a) H；(b) 单价单齿取代基；或：(c) 与相邻的环取代基一起，并且与这些环取代基附着的环原子一起形成融合环的环取代基；以及其药学上可接受的盐、酯、酰胺、溶剂化物、水合物和保护形式。本发明还涉及包含这样的化合物的制药组合物，以及这样的化合物和组合物的使用，无论是体外还是体内，例如在治疗增殖性疾病（例如癌症）和/或由硫代还蛋白/硫代还蛋白还原酶介导的疾病中。
• Quinols as Novel Therapeutic Agents. 2. 4-(1-Arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien-1-ones and Related Agents as Potent and Selective Antitumor Agents
  作者：Jane M. Berry、Tracey D. Bradshaw、Iduna Fichtner、Ruobo Ren、Carl H. Schwalbe、Geoffrey Wells、Eng-Hui Chew、Malcolm F. G. Stevens、Andrew D. Westwell

  DOI：10.1021/jm040859h

  日期：2005.1.1

  A series of substituted 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2, 5-dien-1-ones (indolylquinols) has been synthesized on the basis of the discovery of lead compound la and screened for antitumor activity. Synthesis of this novel series was accomplished via the one-pot" addition of lithiated (arylsulfonyl)indoles to 4,4-dimethoxycyclohexa-2,5-dienone followed by deprotection under acidic conditions. Similar methodology gave rise to the related naphtho-, 1H-indole-, and benzimidazole-substituted quinols. A number of compounds in this new series were found to possess in vitro human tumor cell line activity substantially more potent than the recently reported antitumor 4-substituted 4-hydroxycyclohexa-2,5-dien-1-ones(1) with similar patterns of selectivity against colon, renal, and breast cell lines. The most potent compound in the series in vitro, 4-(1-benzenesulfonyl-6-fluoro-1H-indol-2-yl)-4-hydroxycyclohexa-2,5-dienone (1h), exhibits a mean GI(50) value of 16 nM and a mean LC50 value of 2.24 muM in the NCl 60cell-line screen, with LC50 activity in the HCT 116 human colon cancer cell line below 10 nM. The crystal structure of the unsubstituted indolylquinol la exhibits two independent, molecules. both participating in intermolecular hydrogen bonds from quinol OH to carbonyl O-2 but one OH group also interacts intramolecularly with a sulfonyl O atom. This interaction, which strengthens upon ab initio optimization, may influence the chemical environment. of the bioactive quinol moiety. In vivo, significant antitumor activity was recorded (day 28) in mice bearing subcutaneously implanted MDA-MB-435 xenografts, following intraperitoneal treatment of mice with compound 1a at 50 mg/kg.