5,6-二甲氧基吲哚啉 | 15937-07-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 5,6-二甲氧基吲哚啉
• 中文别名: 2,3-二氢-5,6-二甲氧基-1H-吲哚
• 英文名称: 5,6-dimethoxyindoline
• 英文别名: 5,6-dimethoxy-2,3-dihydro-1H-indole
• CAS: 15937-07-2
• 化学式: C₁₀H₁₃NO₂
• mdl: MFCD09734896
• 分子量: 179.219
• InChiKey: DPRMKYPHVPDUIH-UHFFFAOYSA-N

物化性质

• 熔点：
  105℃ (benzene )
• 沸点：
  301.2±42.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5,6-二甲氧基吲哚啉 在 氢溴酸 作用下， 反应 3.0h， 以62%的产率得到二羟基二氢吲哚
  参考文献：
  名称：

  多巴胺的过氧化物酶/ H2O2氧化产生神经毒素6-羟基多巴胺。

  摘要：

  在生理pH值下，过氧化物酶/ H2O2系统对神经递质多巴胺（DA）的氧化作用除了会导致多巴胺色素和多巴胺醌（DQ）氧化环化产生的5,6-二羟基吲哚外，还会导致大量的神经毒素6-羟基多巴胺（6 -OHDA）的形式为氧化醌类化合物（topaminequinone，TQ）。已表明，TQ的形成主要取决于反应介质中过氧化氢的存在，当使用酪氨酸酶/ O2系统或化学试剂（如高碘酸盐或铁氰化物）进行DA氧化时，未观察到TQ的形成。这些和其他数据表明，在采用的条件下，过氧化氢阴离子对DQ的亲核攻击导致TQ与分子内环化路径显着竞争。按照这种机制，反应过程不受羟基自由基清除剂的存在的影响。如所预期的，N-乙酰基多巴胺模型（1）的过氧化物酶/ H2O2氧化产生的2-羟基-1,4-苯醌3的产率高达55％，具体取决于儿茶酚胺/ H2O2的摩尔比。同样，使4-甲基-1,2-苯醌（4）与过氧化氢反应，以良好的收率得到2-羟基-5-甲基-1

  DOI：

  10.1021/jm00006a010
• 作为产物：
  描述：

  2-(2-溴-4,5-二甲氧基苯基)乙胺盐酸盐 在 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 45.0h， 以36%的产率得到5,6-二甲氧基吲哚啉
  参考文献：
  名称：

  Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

  摘要：

  5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2,3-dimethoxy-benzamide (1) is one of the most potent and selective sigma(2) receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their sigma(1)/sigma(2) binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher sigma(1)/sigma(2) selectivity, derived from a higher sigma(2) affinity and a lower sigma(1) affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional sigma(2) receptor binding affinity and selectivity for this active series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.006

文献信息

• Aerobic Dehydrogenation of <i>N</i> ‐Heterocycles with Grubbs Catalyst: Its Application to Assisted‐Tandem Catalysis to Construct <i>N</i> ‐Containing Fused Heteroarenes
  作者：Daichi Kawauchi、Kenta Noda、Yoshiyuki Komatsu、Kei Yoshida、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1002/chem.202001961

  日期：2020.12.4

  catalyst is developed. The reaction is applicable to various nitrogen‐containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen‐mediated structural change of the Grubbs catalyst, we integrated ring‐closing metathesis and subsequent aerobic

  开发了由Grubbs催化剂催化的含氮杂环的好氧脱氢。该反应适用于各种含氮杂环。未保护的二氢吲哚内酰胺V氧化为吲哚内酰胺V证实了该方法具有极高的官能团相容性。此外，利用氧介导的Grubbs催化剂的结构变化，我们整合了闭环复分解和随后的需氧脱氢以分子氧为化学触发物开发新型辅助串联催化。所述辅助串联催化的效用通过的简明合成证明Ñ含稠合杂芳烃包括天然抗生素，绿脓菌素。
• Synthesis and Biological Evaluation of Nonclassical 2,4-Diamino-5-methylpyrido[2,3-<i>d</i>]pyrimidines with Novel Side Chain Substituents as Potential Inhibitors of Dihydrofolate Reductases
  作者：Aleem Gangjee、Anil Vasudevan、Sherry F. Queener

  DOI：10.1021/jm960734f

  日期：1997.2.1

  Nine novel 2,4-diamino-5-methyl-6-substituted-pyrido[2,3-d]pyrimidines, 2-10, were synthesized as potential inhibitors of Pneumocystis carinii dihydrofolate reductase (pcDHFR) and Toxoplasma gondii dihydrofolate reductase (tgDHFR). Compounds 2-5 were designed as conformationally restricted analogues of trimetrexate (TMQ), in which rotation around tau 3 was constrained by incorporation of the side chain

  合成了9种2,4-二氨基-5-甲基-6-取代的吡啶并[2,3-d]嘧啶2-10作为卡氏肺孢子虫二氢叶酸还原酶（pcDHFR）和弓形体弓形虫二氢叶酸还原酶（tgDHFR）的潜在抑制剂）。化合物2-5被设计为曲美曲塞（TMQ）的构象受限类似物，其中围绕tau 3的旋转通过结合侧链氮作为二氢吲哚或吲哚环的一部分而受到限制。在侧链氮和苯环之间具有额外原子的类似物6，其氮为四氢异喹啉环的一部分。类似物7-9是表柔伯霉素（Ro 11-8958）类似物，并且与吡咯伯胺类似，在苯基环上含有吡咯环作为侧链取代的一部分。设计这些类似物以研究吡咯取代在2,4-二氨基-5-甲基-6-（苯胺基甲基）吡啶并[2,3-d]嘧啶的苯环上的作用。分子模型表明，在侧链苯环邻位的吡咯取代基最有可能与pcDHFR相互作用，其方式与表必隆的吡咯部分相似。合成类似物10，其中苯环取代了甲氧基，以确定苯环对选择性，亲脂性和细胞渗透性的
• [EN] NOVEL PYRAZOLE AND IMIDAZOLE DERIVATIVES USEFUL AS OREXIN ANTAGONISTS<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRAZOLE ET D'IMIDAZOLE UTILES À TITRE D'ANTAGONISTES D'OREXINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2012110986A1

  公开（公告）日：2012-08-23

  The present invention relates to pyrazole and imidazole derivatives of formula (I) wherein U, V, L, X, Y, R1, (R2)n and (R3)m and ring A are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

  本发明涉及式(I)的吡唑和咪唑衍生物，其中U、V、L、X、Y、R1、(R2)n和(R3)m以及环A如描述中所述，其制备方法，其药学上可接受的盐，以及作为药物的用途，含有一个或多个式(I)化合物的药物组合物，特别是作为促进睡眠的药物受体拮抗剂的用途。
• New linear or cyclic ureas
  申请人：——

  公开号：US20010009911A1

  公开（公告）日：2001-07-26

  Compound of formula (I): 1 wherein: V represents a single bond or an alkylene chain, M represents a single bond or an alkylene chain, A and E each represents nitrogen or CH, but at least one of the two groups A or E represents nitrogen, W represents a group of formula (i), (ii) or (iii): 2 wherein: X represents carbonyl, sulphonyl or sulphoxide, G 1 , G 2 and G 3 are as defined in the description, T represents a fused phenyl group or a fused pyridyl group, R 1 represents hydrogen, linear or branched (C 1 -C 6 )alkyl, aryl or aryl-(C 1 -C 6 )alkyl in which the alkyl moiety is linear or branched, R 2a and R 2b , which are the same or different, are as defined in the description, R 3 represents aryl or heteroaryl-A as defined in the description, each of which groups may optionally be substituted, Y represents aryloxy, heteroaryloxy or heteroaryl-B as defined in the description, each of which groups may optionally be substituted, its isomers, its hydrates, its solvates and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in the treatment of diseases or pathological conditions in which endothelial dysfunction is known.

  化合物的化学式（I）如下：其中：V代表单键或烷基链，M代表单键或烷基链，A和E各代表氮或CH，但两个基团A或E中至少有一个代表氮，W代表化学式（i）、（ii）或（iii）中的一个基团：其中：X代表酰基、磺酰基或亚砜基，G1、G2和G3如描述中定义，T代表融合苯基团或融合吡啶基团，R1代表氢、线性或支链（C1-C6）烷基、芳基或芳基-(C1-C6)烷基，其中烷基基团是线性或支链的，R2a和R2b，相同或不同，如描述中定义，R3代表芳基或杂芳基-A如描述中定义，这些基团可以选择性地被取代，Y代表芳氧基、杂芳氧基或杂芳基-B如描述中定义，这些基团可以选择性地被取代，以及其异构体、水合物、溶剂合物及其与药用酸的加合物。含有该化合物的药物产品可用于治疗已知存在内皮功能障碍的疾病或病理状况。
• Indole/indoline based hybrid dyes and indole/indoline based hybrid dye intermediate products
  申请人：——

  公开号：US20040006834A1

  公开（公告）日：2004-01-15

  A composition and method for using the composition for dyeing keratin fibers. The composition consists of indole/indoline hybrid dyes and hybrid dye precursors. More particularly, the indole/indoline hybrid dyes and hybrid dye precursors correspond to formula (I): X—S—Y  (I) where X is a group derived from an indole or indoline derivative as a melanin precursor, Y is a group derived from an oxidation dye precursor of the secondary or primary intermediate type or an indole or indoline derivative as a melanin precursor; and S is a structural element which is common constituent of the groups X and Y, a direct bond or at least one spacer group. The composition may also be used to color human skin.

  一种用于染色角蛋白纤维的组合物和使用该组合物的方法。该组合物由吲哚/吲哚啉混合染料和混合染料前体组成。更具体地说，吲哚/吲哚啉混合染料和混合染料前体对应于式(I)：X—S—Y  (I)，其中X是从吲哚或吲哚啉衍生物作为黑色素前体的基团，Y是从次级或主要中间体的氧化染料前体或吲哚或吲哚啉衍生物作为黑色素前体的基团衍生的基团；S是X和Y基团的共同结构元素，直接键或至少一个间隔基团。该组合物也可用于给人类皮肤着色。