4H-吡咯并[1,2-a]吲哚 | 247-66-5

• 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
• 中文名称: 4H-吡咯并[1,2-a]吲哚
• 英文名称: 9H-pyrrolo<1,2-a>indole
• 英文别名: 9H-pyrrolo-[1,2-a]-indole；1H-pyrrolo[1,2-a]indole；9H-pyrrolo[1,2-a]indole；fluorazene；9H-pyrrolo-[1,2a]-indole；pyrrolo [1,2-a]indole；4H-pyrrolo[1,2-a]indole
• CAS: 247-66-5
• 化学式: C₁₁H₉N
• 分子量: 155.199
• InChiKey: JGCYQWJGSSQVSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  60-65 °C(Press: 0.3 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 熔点：
  88.6-89.6 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4H-吡咯并[1,2-a]吲哚 在 Rh on carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以75%的产率得到1H-吡咯并[1,2-a]吲哚,2,3-二氢-
  参考文献：
  名称：

  2,3-二氢-1 H-吡咯并[1,2- a ]吲哚，2,3-二氢-9-甲基-1 H-吡咯并[1,2- a ]吲哚，1,2,2a的制备，3,4,5-六氢吡咯并[3,2,1- jk ]咔唑和2,3,3a，4,5,6-六氢-1 H-吡啶并[3,2,1- jk ]咔唑

  摘要：

  已经研究了制备标题中列出的四种化合物的几种途径，以决定适合于大量获取材料的方法。

  DOI：

  10.1039/p19800000097
• 作为产物：
  描述：

  fluorazone 在 二乙二醇 作用下， 生成 4H-吡咯并[1,2-a]吲哚
  参考文献：
  名称：

  具有平面刚性电子供体/受体分子的快速分子内电荷转移

  摘要：

  平面刚性分子芴（FPP）在激发态发生快速可逆分子内电荷转移（ICT），在-45℃极性溶剂乙基氰中反应时间为12ps。FPP的ICT态具有偶极矩mu(e)(ICT) 为 13 D，远大于局部激发态 LE (1 D)。FPP 的 ICT 行为与其柔性对应物 N-苯基吡咯 (PP) 的行为相似，其中 mu(e)(ICT) = 12 D。这些结果表明，可以有效地将分子内电荷转移到平面 ICT 状态。因此，在设计能够快速切换的 ICT 系统时，重要的是要认识到不需要大振幅运动，例如形成扭曲的分子内电荷转移 (TICT) 状态所必需的运动。

  DOI：

  10.1021/ja049809s

文献信息

• Cytotoxic N-unsubstituted indoles and cyclopent(b)indoles and method of making and using same
  申请人：——

  公开号：US20040006054A1

  公开（公告）日：2004-01-08

  The merits of N-unsubstituted indoles and cyclopent[b]indoles as DNA-directed reductive alkylating agents are described. These systems represent a significant departure from N-substituted and pyrrolo[1,2-a] fused systems such as the mitomycins and mitosenes. The cyclopent[b]indole—based aziridinylquinone, when bearing an acetate leaving group, was found to be cytotoxic and displayed significant in vivo activity against syngeneic tumor implants. This particular analogue was unexpectedly superior to the others studied, both in terms of high specificity for the activating enzyme DT-diaphorase and in high % DNA alkylation. Alkylation by a quinone methide intermediate as well as by the aziridinyl group were examined for crosslinking. The possible metabolites of the most active indole species were prepared and found to retain cytotoxicity, strongly suggesting that in vivo activity could also be sustained. The indole systems in the present invention display selectivity for melanoma and for non small cell lung, colon, renal, and prostate cancers when administered in an effective amount. The cancer specificity observed is believed to pertain to differential substrate specificity for DT-diaphorase.

  描述了N-未取代吲哚和环戊[b]吲哚作为DNA定向还原烷基化剂的优点。这些体系与N-取代和吡咯[1,2-a]融合体系（如丝菌素和丝菌烯）有显著不同。基于环戊[b]吲哚的氮杂环喹喙醌，当带有乙酸离去基团时，被发现具有细胞毒性，并对同基因肿瘤移植物显示出显著的体内活性。这种特定的类似物在高度特异性激活酶DT-二氧还酶和高DNA烷基化百分比方面意外地优于其他研究过的类似物。通过醌亚甲基中间体和环氧丙基基团进行了交联的烷基化研究。最活跃的吲哚物种的可能代谢产物已经制备并发现保留了细胞毒性，强烈暗示体内活性也可能持续存在。本发明中的吲哚体系在有效剂量下对黑色素瘤和非小细胞肺癌、结肠癌、肾癌和前列腺癌显示出选择性。观察到的癌症特异性被认为与DT-二氧还酶的不同底物特异性有关。
• [EN] FLINDEROLE ANALOGUES AND PROCESS FOR SYNTHESIS THEREOF<br/>[FR] ANALOGUES DE FLINDEROLE ET LEUR PROCÉDÉ DE SYNTHÈSE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012107934A1

  公开（公告）日：2012-08-16

  The present invention discloses flinderole compounds/analogues of formula I and to a process for the preparation of same, comprising stereo- and regioselective [3+2] cycloaddition reaction of a tertiary alcohol (1a') and a sulphonated diene (1b') in presence of Lewis acid selected from Cu(OTf)2 or BF3OEt2 and a non-polar solvent at room temperature. The flinderole compounds /analogues of the instant invention and prepared by the process described therein is represented by the general formula I,(The formula I should be inserted here) wherein R1-R4 are described herein in the specification.

  本发明公开了公式I的flinderole化合物/类似物以及其制备方法，包括在室温下，在Lewis酸Cu(OTf)2或BF3OEt2和非极性溶剂的存在下，对三级醇(1a')和磺化二烯(1b')进行立体和区域选择性的[3+2]环加成反应。本发明的flinderole化合物/类似物由所述方法制备，其通式I表示如下，其中R1-R4在本说明书中描述。
• Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp²)–H Bond Functionalization
  作者：Shuai Xu、Ri Chen、Zihao Fu、Qi Zhou、Yan Zhang、Jianbo Wang

  DOI：10.1021/acscatal.6b03562

  日期：2017.3.3

  A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C–C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source

  已经开发出了一种高效且操作简单的钯催化的正[4 +1]环化反应。该反应的特征是在羧基中心上形成两个不同的C–C键。它代表了一种简便的方法，用于合成多种多环芳烃（PAH）和1 H-茚，并以易于获得的（三甲基甲硅烷基）重氮甲烷作为卡宾源。金属卡宾迁移插入和C（sp 2）–H键活化被提议为该转变的关键步骤。该反应进一步证明了与各种过渡金属催化的转化结合的基于卡宾的偶联的多功能性。
• N-Fused Indolines through Non-Carbonyl-Stabilized Rhodium Carbenoid CH Insertion of N-Aziridinyl Imines
  作者：Stuart J. Mahoney、Eric Fillion

  DOI：10.1002/chem.201103155

  日期：2012.1.2

  Under rhodium catalysis, N‐aziridinyl imines provided access to N‐fused indolines through non‐carbonyl‐stabilized rhodium carbenoid CH insertion. The utility of this methodology for the synthesis of architecturally complex heterocycles was further demonstrated by an expedient total synthesis of (±)‐cryptaustoline (see scheme).

  下铑催化，Ñ提供给访问吖丙啶基亚胺Ñ通过非羰基稳定化-融合二氢吲哚铑卡宾体Ç  ħ插入。方便的全合成（±）-密码啉（参见方案）进一步证明了该方法在合成复杂的杂环结构中的实用性。
• NOVEL DERIVATIVES OF PYRROLOINDOLE WHICH ARE INHIBITORS OF HSP90, COMPOSITIONS CONTAINING SAME, AND USE THEREOF
  申请人：Alasia Marcel

  公开号：US20110184015A1

  公开（公告）日：2011-07-28

  Pyrroloindoles of formula (I) are provided wherein Het is an aromatic or partially unsaturated, monocyclic or bicyclic heterocycle containing between 1 and 4 heteroatoms N, O or S, optionally substituted by R1 or R′1 which are the same or different; R is X-(A-B)n-CONH2, X-(A-B)n-O—CONH2, X-(A-B)n-NH—CONH2, X—(CH2)m-heterocycloalkyl, X(CH2)m-aryl and X—(CH2)m-heteroaryl wherein X is —O—C(O), —NH—C(O), NH—CS, —NH—CO—CH2-O—; —NH—COCH2-S—CH2-CO—NH—; —NH—CO—(CH2)2-SO2-; and —NH—CO—CH2-N(CH3)-CO—; A and B are the same or different and are each independently a single bond, CH2, CH-alkyl, and CH-aralkyl; n=1,2 and m=0, 1; R1 and/or R′1 are H, halogen, CF3, nitro, cyano, alkyle, hydroxy, mercapto, amino, alkylamino, dialkylamino, alkoxy, alkylthio, and carboxy, free or esterified by an alkyl, carboxamide, CONH(alkyl), CON(alkyl)2, NH—CO-alkyl, sulfonamide, NH—SO2-alkyl, S(O)2-NHalkyl, and S(O2)-N(alkyl)2 group, all of said alkyl, alcoxy and alkylthio groups being optionally substituted themselves, said products being in all isomer forms and salts, as medicaments.

  提供了式（I）的吡咯吲哚，其中Het是含有1至4个杂原子N、O或S的芳香或部分不饱和的单环或双环杂环，可以由R1或R′1取代，它们可以相同也可以不同；R是X-(A-B)n-CONH2，X-(A-B)n-O—CONH2，X-(A-B)n-NH—CONH2，X—(CH2)m-杂环烷基，X(CH2)m-芳基和X—(CH2)m-杂芳基，其中X是—O—C(O)，—NH—C(O)，NH—CS，—NH—CO—CH2-O—；—NH—COCH2-S—CH2-CO—NH—；—NH—CO—(CH2)2-SO2-；和—NH—CO—CH2-N(CH3)-CO—；A和B相同或不同，分别是单键，CH2，CH-烷基和CH-芳烷基；n=1,2，m=0,1；R1和/或R′1是H，卤素，CF3，硝基，氰基，烷基，羟基，巯基，氨基，烷基氨基，二烷基氨基，烷氧基，烷基硫基和羧基，均为自由或被烷基、羧酰胺、CONH(烷基)、CON(烷基)2、NH—CO-烷基、磺酰胺、NH—SO2-烷基、S(O)2-NH烷基和S(O2)-N(烷基)2基酯化的，所述的所有烷基、烷氧基和烷基硫基基团本身也可以被取代，所述产品以所有异构体形式和盐形式作为药物。