3a,4,5,6-四氢琥珀酰亚胺并(3,4-b)-苊-10-酮 | 4756-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 3a,4,5,6-四氢琥珀酰亚胺并(3,4-b)-苊-10-酮
• 中文别名: 3A,4,5,6-四氢琥珀酰亚胺基[3,4-B]苊-10-酮
• 英文名称: 3a,4,5,6-tetrahydrosuccinimido<3,4-b>acenaphthen-10-one
• 英文别名: 3a,4,5,6-tetrahydrosuccinimido[3,4-b]acenapthen-10-one；5,6-dihydro-4H-acenaphtho[1,8a-c]pyrrole-1,3,10-trione；3a,4,5,6-tetrahydrosuccinimido[3,4-b]acenaphthen-10-one；5,6-Dihydro-1H,4H-acenaphtho(1,8a-c)pyrrole-1,3,10(2H,10aH)-trione；13-azatetracyclo[7.5.1.01,11.05,15]pentadeca-5(15),6,8-triene-10,12,14-trione
• CAS: 4756-92-7
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: KWUXACIWMYKRCI-UHFFFAOYSA-N

物化性质

• 熔点：
  250-254 °C(lit.)
• 沸点：
  538.4±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3a,4,5,6-四氢琥珀酰亚胺并(3,4-b)-苊-10-酮 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,10a-dimethyl-3a,4,5,6-tetrahydrosuccinimido<3,4-b>acenaphthen-10-one
  参考文献：
  名称：

  Campaigne, E.; Huffman, J. C.; Yodice, Richard, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 135 - 142

  摘要：

  DOI：

文献信息

• Synthesis and serotonergic activity of a series of 2-(N-benzyl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives: novel antagonists for the vascular 5-HT1B-like receptors
  作者：Gerard P. Moloney、Graeme R. Martin、Neil Mathews、Heather Hobbs、Susan Dodsworth、Pang Yih Sang、Cameron Knight、Miles Maxwell、Robert C. Glen

  DOI：10.1039/a903141c

  日期：——

  The synthesis and vascular 5-HT1B-like receptor activity of a novel series of 2-(N-benzyl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives is described. Modifications to the 5-ethylene linked heterocycle are explored. Compounds such as N-benzyl-5-[2-(phthalimido)ethyl]-3-[2-(dimethylamino)ethyl]-1H-indole-2-carboxamide 22 (pKB = 7.33), the 2-aminobenzyl analogue 24 (pKB = 7.19), which both contain a phthalimide group, and N-benzyl-5-[2-(1-benzyl-2,5-dioxoimidazolidin-4-yl)ethyl]-3-[2-(dimethylamino)ethyl]-1H-indole-2-carboxamide 81 (pKB = 7.05), which incorporates an N-benzylhydantoin moiety, have good 5-HT1B-like affinity and indicate that there may be a hydrophobic binding pocket within the vascular 5-HT1B-like receptor previously not considered. Compounds including N-benzyl-3-[2-(dimethylamino)ethyl]-5-[2-(2,4-dioxo-1,3-thiazolidinyl)ethyl]-1H-indole-2-carboxamide 39 (pKB = 7.35) and the dimethyl analogue 46 (pKB = 7.48) which contain a 2,4-thiazolidinedione moiety have good vascular 5-HT1B-like receptor affinity and show that the sulfur atom is well tolerated. Compound 61 which includes a methylsulfonyl substituent on the 1-nitrogen of the hydantoin ring system has the highest recorded 5-HT1B-like affinity for this series (pKB = 7.54) and it is proposed that this functional group can interact with a secondary hydrogen bonding region within the receptor. Compounds 22, 24, 39, 46, 61 and 81 also exhibited good selectivity over the α1-adrenoceptors. The most selective compound from this series is 46 which contains a 5,5-dimethylthiazolidine-2,4-dione group and which is 66-fold selective over the α1-adrenoceptors. This finding is consistent with the previous discovery that 5,5-dimethyl substitution on the hydantoin group in a related series of compounds afforded superior selectivity for 5-HT1B-like receptors over α1-adrenoceptors and other 5-HT receptors, in particular 5-HT2A receptors, relative to unsubstituted hydantoin analogues. The selectivity of these compounds for the vascular 5-HT1B-like receptor is discussed. Structure–activity relationship indicated a significant steric requirement of the 5-HT1B-like receptor subtype. Potential modes of binding for several of the compounds to a vascular 5-HT1B-like receptor pharmacophore model are also proposed.

  0)。
• Cyclic imide-substituted pyridylalkane, alkene, alkine carboxamides useful as cytostatic and immunosuppressive agents
  申请人：Astellas Pharma GmbH

  公开号：US07192967B1

  公开（公告）日：2007-03-20

  The invention relates to new pyridylalkane, alkene, and alkine carboxamides substituted with an imide with a saturated or one or several-fold unsaturated hydrocarbon residue in the carboxylic acid group according to general formula (I), wherein the residue E is a cyclic imide, methods for the production of these compounds, medicaments containing these and their production as well as their therapeutic use, especially as cytostatic agents and immunosuppressive agents, for example in the treatment or prevention of various types of tumors, inhibition of abnormal cell growth and control of immune reactions, for example autoimmune diseases.

  本发明涉及一种新的吡啶基烷基，烯基和炔基羧酰胺，其在羧酸基中带有饱和或一种或多种不饱和的碳氢残基的酰胺衍生物，该化合物的一般式（I）中残基E为环状酰亚胺，制备这些化合物的方法，含有这些化合物的药物及其制备以及它们的治疗用途，特别是作为细胞毒性剂和免疫抑制剂，例如用于治疗或预防各种类型的肿瘤，抑制异常细胞生长和控制免疫反应，例如自身免疫性疾病。
• CYCLIC IMIDE-SUBSTITUTED PYRIDYLALKANE, ALKENE, AND ALKINE CARBOXAMIDES USEFUL AS CYTOSTATIC AND IMMUNOSUPPRESSIVE AGENTS
  申请人：Klinge Pharma GmbH

  公开号：EP1042315B1

  公开（公告）日：2004-04-14
• Tertiary phosphine complexes of gold(I) and gold(III) with imido ligands: 1H, 31P, and 15N NMR spectroscopy, antiinflammatory activity, and x-ray crystal structure of (phthalimido)(triethylphosphine)gold(I)
  作者：Susan J. Berners Price、Michael J. DiMartino、David T. Hill、Reiko Kuroda、Muhammed A. Mazid、Peter J. Sadler

  DOI：10.1021/ic00215a026

  日期：1985.10
• USE OF VITAMIN PP COMPOUNDS
  申请人：Klinge Pharma GmbH

  公开号：EP1079832B1

  公开（公告）日：2005-11-30

表征谱图