5-[(1H-indol-3-yl)methylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione | 24774-42-3

• 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: 5-[(1H-indol-3-yl)methylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione
• 英文别名: 5-((1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione；5-(1H-indol-3-ylmethylene)-pyrimidine-2,4,6-trione；5-(1H-indol-3-ylmethylene)pyrimidine-2,4,6-trione；5-((1H-indol-3-yl)methylidene)barbituric acid；5-indol-3-ylmethylene-pyrimidine-2,4,6-trione；5-indol-3-ylmethylene-barbituric acid；5-(1H-indol-3-ylmethylidene)-1,3-diazinane-2,4,6-trione
• CAS: 24774-42-3
• 化学式: C₁₃H₉N₃O₃
• mdl: MFCD00118194
• 分子量: 255.233
• InChiKey: FIJMDYJMWFWCIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.06
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-[(1H-indol-3-yl)methylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione 在 5%-palladium/activated carbon 氢气 作用下， 以 甲醇 、 苯 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 4.0h， 生成 5-(3-Indolylmethyl)barbituric acid
  参考文献：
  名称：

  在铂和钯催化剂的存在下，用羰基化合物对巴比妥酸衍生物进行还原性C-烷基化

  摘要：

  有效的单-和二-制备合成程序Ç通过钯和巴比土酸溶液的铂催化氢化烷基化巴比土酸衍生物（未取代的，Ñ -单和Ñ，N'二取代的巴比土酸）和羰基化合物（脂族和芳族醛和酮）。

  DOI：

  10.1016/s0040-4039(01)00621-9
• 作为产物：
  描述：

  3-吲哚甲醛 、 巴比妥酸 在 iron(III) chloride hexahydrate 、 水 作用下， 反应 0.58h， 以85%的产率得到5-[(1H-indol-3-yl)methylidene]-2,4,6(1H,3H,5H)-pyrimidinetrione
  参考文献：
  名称：

  Reaction of 6-aminouracils with aldehydes in water as both solvent and reactant under FeCl₃·6H₂O catalysis: towards 5-alkyl/arylidenebarbituric acids

  摘要：

  5-烷基/芳基亚甲基巴比妥酸通过FeCl₃·6H₂O催化的6-氨基尿嘧啶、水和醛的多米诺反应高效合成，其中水既充当溶剂又作为反应物，在温和条件下进行。

  DOI：

  10.1039/c4ra03413a

文献信息

• Dimethylamine substitution in N , N -dimethyl enamines. Synthesis of aplysinopsin analogues and 3-aminotetrahydrocoumarin derivatives
  作者：Lovro Selič、Branko Stanovnik

  DOI：10.1016/s0040-4020(01)00174-0

  日期：2001.4

  Some new six-membered aplysinopsin analogues were prepared from 5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetriones and indole derivatives. Also 2-[[(2,4,6-trioxohexahydropyrimidin-5-ylidene)methyl]amino]-3-dimethylaminopropenoates were synthesized and employed in the synthesis of fused 2H-pyran-2-ones.

  从5-二甲基氨基亚甲基-2,4,6（1 H，3 H，5 H）-嘧啶三酮和吲哚衍生物制备了一些新的六元皂苷类似物。还合成了2-[[（（2,4,6-三氧六氢嘧啶-5-亚甲基）甲基]氨基] -3-二甲基氨基丙酸酯，并将其用于稠合的2 H-吡喃-2-酮的合成中。
• A simple method for knoevenagel condensation of α,β-conjugated and aromatic aldehydes with barbituric acid
  作者：Branko S. Jursic

  DOI：10.1002/jhet.5570380318

  日期：2001.5

  Several aromatic and α,β-conjugated aromatic aldehydes were condensed with barbituric acid in methanol solution in the absence of acid or base as a catalyst, affording 5-ylidenebarbituric acid derivatives in almost quantitative yields.

  在不存在酸或碱作为催化剂的情况下，将几种芳族和α，β-共轭芳族醛与巴比妥酸在甲醇溶液中缩合，以几乎定量的产率提供5-亚烷基巴比妥酸衍生物。
• Facile Synthesis and Biological Evaluation of Substituted 5-(1H-Indol-3-ylmethylene) pyrimidine-2,4,6-trione Derivatives Using L-Tyrosine in Aqueous Medium
  作者：G. Thirupathi、P.K. Dubey、Y. Bharathi Kumari

  DOI：10.14233/ajchem.2013.15364

  日期：——

  L-Tyrosine as an efficient catalyst for the Knoevenagel condensation of substituted indole-3-aldehydes 1(a-d), N-methyl indole-3-aldehydes 4(a-d), N-ethyl indole-3-aldehydes 6(a-d) with barbituric acid (2) containing cyclic active methylene group to produce 3(a-d), 5(a-d) and 7(a-d), respectively in water at room temperature for 10 min. The antimicrobial activities of 3(a-d), 5(a-d) and 7(a-d) have been studied.

  L-酪氨酸作为一种高效催化剂，促进取代的吲哚-3-醛1(a-d)、N-甲基吲哚-3-醛4(a-d)、N-乙基吲哚-3-醛6(a-d)与含有环状活性亚甲基基团的巴比妥酸（2）在室温下水相中反应10分钟，生成3(a-d)、5(a-d)和7(a-d)。已研究了3(a-d)、5(a-d)和7(a-d)的抗菌活性。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Design, synthesis and anticancer activities of hybrids of indole and barbituric acids—Identification of highly promising leads
  作者：Palwinder Singh、Matinder Kaur、Pooja Verma

  DOI：10.1016/j.bmcl.2009.04.014

  日期：2009.6

  By combining the structural features of indole and barbituric acid, new hybrid molecules were designed and synthesized. Evaluations of these molecules over 60 cell line panel of human cancer cells have identified two molecules with significant anticancer activities. Dockings of two active molecules in the active sites of COX-2, thymidylate synthase and ribonucleotide reductase indicate their strong interactions with these enzymes. (C) 2009 Elsevier Ltd. All rights reserved.