1-methyl-6-indolylethylamine | 74631-89-3

• 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: 1-methyl-6-indolylethylamine
• 英文别名: 2-(1-methyl-1H-indol-6-yl)ethan-1-amine；2-(1-Methyl-1H-indol-6-yl)ethanamine；2-(1-methylindol-6-yl)ethanamine
• CAS: 74631-89-3
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: DOZZBMFQPOGSQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  31
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-6-indolylethylamine 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1,5,6,7,8,9-hexahydro-1-methyl-6-oxoazepino<4,5-f>indole
  参考文献：
  名称：

  Photochemical synthesis of azepinoindoles and azocinoindoles from N-chloroacetylindolylethylamines, and a mechanistic study based on the correlation between quantum yields and calculated frontier electron densities of indole radicals.

  摘要：

  在 50% 的乙醇水溶液中照射时，七种吲哚乙胺异构体的 N-氯乙酰基衍生物通过正位和周位的光环化反应生成相应的偶氮吲哚衍生物。在 2537 Å 光下生成产物的量子产率显示，吲哚环各位置的相对反应性依次为 3>6、4>7、2>5>1。为了确定反应的中间产物并确定光环化的机理，利用 CNDO/2 和 INDO 计算了几种吲哚的前沿电子密度。1 取代吲哚衍生物生成产物的量子产率与 1 甲基吲哚自由基阳离子的单占分子轨道（SOMO）电子密度（ED）有相当好的相关性（相关系数 r=0.82），但 1 未取代化合物生成产物的量子产率与吲哚-1-自由基的 SOMO-ED 有更好的相关性（r=0.90）。这些结果表明，N-氯乙酰吲哚乙胺的光环化机理涉及吲哚自由基阳离子和作为反应中间体的吲哚-1-自由基。

  DOI：

  10.1248/cpb.28.900
• 作为产物：
  描述：

  N-<2-(1-methylindol-6-yl)ethyl>acetamide 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 以2.2 g的产率得到1-methyl-6-indolylethylamine
  参考文献：
  名称：

  Photochemical synthesis of azepinoindoles and azocinoindoles from N-chloroacetylindolylethylamines, and a mechanistic study based on the correlation between quantum yields and calculated frontier electron densities of indole radicals.

  摘要：

  在 50% 的乙醇水溶液中照射时，七种吲哚乙胺异构体的 N-氯乙酰基衍生物通过正位和周位的光环化反应生成相应的偶氮吲哚衍生物。在 2537 Å 光下生成产物的量子产率显示，吲哚环各位置的相对反应性依次为 3>6、4>7、2>5>1。为了确定反应的中间产物并确定光环化的机理，利用 CNDO/2 和 INDO 计算了几种吲哚的前沿电子密度。1 取代吲哚衍生物生成产物的量子产率与 1 甲基吲哚自由基阳离子的单占分子轨道（SOMO）电子密度（ED）有相当好的相关性（相关系数 r=0.82），但 1 未取代化合物生成产物的量子产率与吲哚-1-自由基的 SOMO-ED 有更好的相关性（r=0.90）。这些结果表明，N-氯乙酰吲哚乙胺的光环化机理涉及吲哚自由基阳离子和作为反应中间体的吲哚-1-自由基。

  DOI：

  10.1248/cpb.28.900

文献信息

• [EN] PYRIMIDINE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE PYRIMIDINE UTILISÉS EN TANT QUE MODULATEURS DES RÉCEPTEURS DES PGE2
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210988A1

  公开（公告）日：2018-11-22

  The present invention relates to pyrimidine derivatives of formula (I) wherein (R1)n, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, 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 modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式(I)的嘧啶衍生物，其中(R1)n，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，以及它们通过调节免疫反应，包括肿瘤中免疫系统的再激活，用于治疗癌症。本发明进一步涉及新颖的苯并呋喃和苯并噻吩衍生物式(II)，及其作为药物的使用，其制备，药用可接受的盐，及其作为药物的使用，以及包含式(I)中一个或多个化合物的药物组合物，尤其是它们作为前列腺素2受体EP2和/或EP4的调节剂的使用。
• Heterocyclic compounds for the treatment of migraine
  申请人：NPS ALLELIX BIOPHARMACEUTICALS, INC.

  公开号：US20040167158A1

  公开（公告）日：2004-08-26

  Described herein are compounds useful in the treatment of migraine, which have the general formula: 1 wherein: W is a CH group or a N atom; Z is N or C-R4; B and D are selected independently from CH and N, with the proviso that at least one of B and D is CH and with the further proviso that one of B and D can represent N only when W and Z are both other than N; A is a group of Formula II, III or IV, such that group A contains at least 1 N atom; NR7 is either —NH— or —N═ is a single or double bond; X is a N atom, a CH group or a C(OH) group when is a single bond; or, when is a double bond, a C atom; Y is an NH, N-alkyl, N-benzyl or CH 2 group; U and V each represent a N atom or a CH group, with the proviso that both cannot be N; a and b are, independently, 0 or 1; c is an integer from 0 to 3; d is an integer from 1 to 3; e is an integer from 1 to 2; f is an integer from 0 to 3; g is an integer from 3 to 6 and h is an integer from 2 to 3; such that the sum of c and d is at least 2 and the sum of e and f is at least 2; R 1 is selected from the group consisting of H, alkyl, alkyloxy, alkanoyl, aminoalkylenyl, alkylaminoalkylenyl, a hydroxyalkylenyl group, an alkyloxyalkylenyl group, a cycloalkyl group, a cycloalkylalkylenyl group, a heterocycloalkyl group, a heterocycloalkylalkylenyl group, an aryl group, a heterocycloaryl group, an amido group, a thioamido group, an arylcarbonyl group and an arylsulfonyl group; R 2 and R 3 are independently selected from the group consisting of H, alkyl, cycloalkyl, alkenyl and optionally-substituted benzyl; or R 2 and R 3 , together with the nitrogen atom to which they are attached, may form a mono- or bi-cyclic group containing up to 10 carbon atoms and which, in addition, may contain a second heteroatom selected from the group consisting of N, S and O, and which may contain one or more substituents selected from the group consisting of alkyl, hydroxy, hydroxymethyl, alkyloxymethyl, amino and substituted amino; R 4 is selected from the group consisting of H, alkyl and cycloalkyl; CR 5 represents a group selected from —CH2—, CH(OH)—, —C(O)—, —CH(alkyl)- and —CH(alkyloxy)-; R6 is selected from the group consisting of H, alkyl, aryl, halogen, hydroxy, alkyloxy, amino, monoalkylamino and di-substitutedalkylamino; and salts and solvates thereof

  本文描述了治疗偏头痛的化合物，其具有以下通式：1其中：W是CH基团或N原子；Z是N或C-R4；B和D独立地选自CH和N，但至少其中之一为CH，并进一步规定当W和Z都不是N时，B和D中的一个可以表示N；A是公式II、III或IV的基团，使得基团A至少包含1个N原子；NR7是—NH—或—N═；is a single or double bond；当is a double bond时，X是C原子；Y是NH、N-烷基、N-苯甲基或CH2基团；U和V分别表示N原子或CH基团，但两者不能同时为N；a和b独立地为0或1；c是0到3之间的整数；d是1到3之间的整数；e是1到2之间的整数；f是0到3之间的整数；g是3到6之间的整数；h是2到3之间的整数；使得c和d的和至少为2，e和f的和至少为2；R1选自H、烷基、烷氧基、烷酰基、氨基烷基亚烷基、烷基氨基烷基亚烷基、羟基烷基亚烷基、烷氧基烷基亚烷基、环烷基、环烷基烷基亚烷基、杂环烷基、杂环烷基烷基亚烷基、芳基、杂环芳基、酰胺基、硫酰胺基、芳基羰基和芳基磺酰基的群；R2和R3独立地选自H、烷基、环烷基、烯基和可选取代苄基的群；或者R2和R3与它们所连接的氮原子一起，可以形成一个含有最多10个碳原子的单环或双环基团，此外，该基团还可以含有从N、S和O组成的第二个杂原子，以及从烷基、羟基、羟甲基、烷氧甲基、氨基和取代氨基的群中选择的一个或多个取代基；R4选自H、烷基和环烷基；CR5表示选自—CH2—、CH(OH)—、—C(O)—、—CH(烷基)-和—CH(烷氧基)-的基团；R6选自H、烷基、芳基、卤素、羟基、烷氧基、氨基、单烷基氨基和二取代烷基氨基的群；以及其盐和溶剂络合物。
• Tricyclic Benzopyrane Compound as Anti-Arrhythmic Agents
  申请人：Ohrai Kazuhiko

  公开号：US20080004262A1

  公开（公告）日：2008-01-03

  This invention relates to benzopyran derivatives of formula (I) or (II), or pharmaceutically acceptable salts thereof wherein R 1 and R 2 are independently of each other hydrogen atom, C 1-6 alkyl group or C 6-14 aryl group, R 3 is hydrogen atom or C 1-6 alkylcarbonyloxy group, or together with R 4 forms a bond, R 4 is hydrogen atom, or together with R 3 forms a bond, m is an integer of 0 to 4, n is an integer of 0 to 4, V is a single bond, CR 7 R 8 , NR 9 , O, S, SO or SO 2 , R 5 is hydrogen atom or C 1-6 alkyl group, R 6 is hydrogen atom, C 1-6 alkyl group, C 3-8 cycloalkyl group, C 3-8 cycloalkenyl group, amino group, C 1-6 alkylamino group, di-C 1-6 alkylamino group, C 6-14 arylamino group, C 2-9 heteroarylamino group, C 6-14 aryl group, C 2-9 heteroaryl group or C 2-9 heterocyclyl group, A is 5-, 6- or 7-member ring fused with benzene ring, as constituent atom of the ring, oxygen atom, nitrogen atom or sulfur atom may be contained in the number of 1 to 3 alone or in a combination thereof, the number of unsaturated bond in the ring is 1, 2 or 3 including an unsaturated bond of the benzene ring to be fused, carbon atoms constituting the ring may be carbonyl or thiocarbonyl. These compounds are useful as an anti-arrhythmic agent.

  本发明涉及式（I）或（II）的苯并吡喃衍生物，或其药学上可接受的盐，其中R1和R2独立地为氢原子，C1-6烷基或C6-14芳基；R3为氢原子或C1-6烷基羰氧基，或与R4一起形成键；R4为氢原子，或与R3一起形成键；m为0至4的整数，n为0至4的整数，V为单键，CR7R8，NR9，O，S，SO或SO2；R5为氢原子或C1-6烷基，R6为氢原子，C1-6烷基，C3-8环烷基，C3-8环烯基，氨基，C1-6烷基氨基，二C1-6烷基氨基，C6-14芳基氨基，C2-9杂芳基氨基，C6-14芳基，C2-9杂芳基或C2-9杂环烷基；A为与苯环融合的5、6或7元环，作为环的组成原子，其中单独或组合存在1至3个氧原子、氮原子或硫原子，环中不饱和键的数量为1、2或3，包括与苯环融合的不饱和键，构成环的碳原子可以是羰基或硫代羰基。这些化合物可用作抗心律失常药物。
• INDOLES AND INDAZOLES FOR THE TREATMENT OF MIGRAINE
  申请人：NPS Allelix Corp.

  公开号：EP1196380A2

  公开（公告）日：2002-04-17
• TRICYCLIC BENZOPYRAN COMPOUND AS ANTI-ARRHYTHMIC AGENTS
  申请人：Nissan Chemical Industries, Ltd.

  公开号：EP1732929B1

  公开（公告）日：2010-10-20