5-((1H-indol-3-yl)methylene)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione | 53215-61-5

• 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
• 英文名称: 5-((1H-indol-3-yl)methylene)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione
• 英文别名: 5-(1H-indol-3'-ylmethylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione；5-((1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione；5-(1H-indol-3-ylmethylene)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione；5-indol-3-ylmethylene-2-thioxo-dihydro-pyrimidine-4,6-dione；5-indol-3-ylmethylene-2-thio-barbituric acid；5-Indol-3-ylmethylen-2-thio-barbitursaeure；5-(1H-indol-3-ylmethylidene)-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 53215-61-5
• 化学式: C₁₃H₉N₃O₂S
• 分子量: 271.299
• InChiKey: XQPSWDRJQACIFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 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：
  73.99
• 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)methylene)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione 在 aluminum oxide 、 盐酸羟胺 作用下， 反应 0.05h， 以83%的产率得到3-(1H-indol-3-yl)-6-sulfanylidene-3,3a-dihydro-1H-[1,2]oxazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Alumina Catalyzed Synthesis of Fused Thioxopyrimidine Derivatives Under Microwaves

  摘要：

  An expeditious solventless approach for the synthesis of pyrazolino[3,4-d]/isoxazolino[3,4-d]/pyrano[2,3-d]/iminopyrimidino[4,5-d]/thioxopyrimidino[4,5-d]/thiazino[5,4-d] pyrimidines from 2-thiobarbituric acid using supported reagents (acidic/basic alumina) under microwave irradiation (MWI) is described. The reaction times were brought down from hours to minutes with yield enhancement. Also the procedure highlights the versatility of solid supports.

  DOI：

  10.1081/scc-120025184
• 作为产物：
  描述：

  3-吲哚甲醛 、 4,6-二羟基-2-巯基嘧啶 以 乙醇 、 水 为溶剂， 反应 6.0h， 以93.3%的产率得到5-((1H-indol-3-yl)methylene)-dihydro-2-thioxopyrimidine-4,6(1H,5H)-dione
  参考文献：
  名称：

  발모촉진용 조성물

  摘要：

  本发明涉及一种新的巴比妥酸（Barbiturate）和硫代巴比妥酸（thiobarbiturate）衍生物以及它们用于促进头发生长的组合物，所述的巴比妥酸（Barbiturate）和硫代巴比妥酸（thiobarbiturate）衍生物不仅可以促进动物模型中的毛发生长，还可以通过促进Wnt/β-连环蛋白和毛发生长因子的信号传导调节，抑制细胞凋亡机制，从而促进头发生长，显示出优异的促发效果，因此，本发明的巴比妥酸（Barbiturate）和硫代巴比妥酸（thiobarbiturate）衍生物可用作促进头发生长的组合物。

  公开号：

  KR101732929B1

文献信息

• Barbituric acid analogs as therapeutic agents
  申请人：——

  公开号：US20030229108A1

  公开（公告）日：2003-12-11

  This invention pertains to active barbituric acid analogs which inhibit HIF-1 activity (e.g., the interaction between HIF-1&agr; and p300) and thereby inhibit angiogenesis, tumorigensis, and proliferative conditions, such as cancer. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit HIF-1 activity, and to inhibit angiogensis, tumorigensis, and proliferative conditions, such as cancer.

  这项发明涉及活性巴比妥酸类似物，其抑制HIF-1活性（例如，HIF-1α与p300之间的相互作用），从而抑制血管生成、肿瘤发生和增生性疾病，如癌症。本发明还涉及包括这些化合物的药物组合物，以及在体外和体内使用这些化合物和组合物来抑制HIF-1活性，以及抑制血管生成、肿瘤发生和增生性疾病，如癌症。
• 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。
• Combination therapy to enhance the anticancer efficacy of platinum drugs
  申请人：University of Pittsburgh-of the Commonwealth System of Higher Education

  公开号：US10478437B2

  公开（公告）日：2019-11-19

  The present invention relates to compositions and methods for reducing cell proliferation and/or promoting cell death. It is based, at least in part, on the discovery that in platinum drug-resistant cell lines, certain compounds, together with a second antiproliferative agent (e.g., cisplatin), act synergistically to promote apoptosis. Accordingly, the present invention provides for novel anticancer strategies.

  本发明涉及减少细胞增殖和/或促进细胞死亡的组合物和方法。本发明至少部分基于以下发现：在铂类药物耐药细胞系中，某些化合物与第二种抗增殖剂（如顺铂）一起发挥协同作用，促进细胞凋亡。因此，本发明提供了新的抗癌策略。
• Synthesis and structure–activity relationship of thiobarbituric acid derivatives as potent inhibitors of urease
  作者：Khalid Mohammed Khan、Fazal Rahim、Ajmal Khan、Muhammad Shabeer、Shafqat Hussain、Wajid Rehman、Muhammad Taha、Momin Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2014.05.057

  日期：2014.8

  A series of thiobarbituric acid derivatives 1-27 were synthesized and evaluated for their urease inhibitory potential. Exciting results were obtained from the screening of these compounds 1-27. Compounds 5, 7, 8, 11, 16, 17, 22, 23 and 24 showed excellent urease inhibition with IC50 values 18.1 ± 0.52, 16.0 ± 0.45, 16.0 ± 0.22, 14.3 ± 0.27, 6.7 ± 0.27, 10.6 ± 0.17, 19.2 ± 0.29, 18.2 ± 0.76 and 1.61 ± 0.18 μM, respectively, much better than the standard urease inhibitor thiourea (IC₅₀=21 ± 0.11 μM). Compound 3, 4, 10, and 26 exhibited comparable activities to the standard with IC₅₀ values 21.4 ± 1.04 and 21.5 ± 0.61 μM, 22.8 ± 0.32, 25.2 ± 0.63, respectively. However the remaining compounds also showed prominent inhibitory potential The structure-activity relationship was established for these compounds. This study identified a novel class of urease inhibitors. The structures of all compounds were confirmed through spectroscopic techniques such as EI-MS and (1)H NMR.
• Solvent-free, microwave assisted Knoevenagel condensation of novel 2,5-disubstituted indole analogues and their biological evaluation
  作者：J.S. Biradar、B.S. Sasidhar

  DOI：10.1016/j.ejmech.2011.10.004

  日期：2011.12

  A rapid, efficient and environmental benign methodology for the preparation of 2,5-disubstituted indole analogues is developed. 2,5-Disubstituted indole-3-carboxaldehydes (1a-c) undergo Knoevenagel condensation with barbiturates (2 & 4), thiazolidine-2,4-dione (6) and 3-methyl-1H-pyrazol-5(4H)-one (8) in solvent-free, NH4OAc catalyzed, microwave assisted reaction. Structures of the products thus obtained were confirmed by their m.p, Elemental analysis, IR. H-1 NMR, C-13 NMR and Mass spectral data. The in vitro antioxidant and cytotoxic activities against three tumor cell lines were evaluated and discussed in terms of their structural differences. Among the screened compounds 9b, 9c, 7b and 5b exhibited excellent antioxidant activity. Compounds 9b, 9c and 7b have shown strong cytotoxicity among the compounds tested. (C) 2011 Elsevier Masson SAS. All rights reserved.