1,3-di-n-propyl-5,6-diamino-2-thiouracil | 121543-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-di-n-propyl-5,6-diamino-2-thiouracil
• 英文别名: 5,6-diamino-1,3-dipropyl-2-thiouracil；5,6-diamino-1,3-dipropyl-2-sulfanylidenepyrimidin-4-one
• CAS: 121543-23-5
• 化学式: C₁₀H₁₈N₄OS
• 分子量: 242.345
• InChiKey: OSHOASUQHIDCOV-UHFFFAOYSA-N

物化性质

• 沸点：
  321.4±52.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-di-n-propyl-5,6-diamino-2-thiouracil 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1,3-dipropyl-8-(2-thienyl)-2-thioxanthine
  参考文献：
  名称：

  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors

  摘要：

  Sulfur-containing analogues of 8-substituted xanthines were prepared in an effort to increase selectivity or potency as antagonists at adenosine receptors. Either cyclopentyl or various aryl substituents were utilized at the 8-position, because of the association of these groups with high potency at A1-adenosine receptors. Sulfur was incorporated on the purine ring at positions 2 and/or 6, in the 8-position substituent in the form of 2- or 3-thienyl groups, or via thienyl groups separated from an 8-aryl substituent through an amide-containing chain. The feasibility of using the thienyl group as a prosthetic group for selective iodination via its Hg2+ derivative was explored. Receptor selectivity was determined in binding assays using membrane homogenates from rat cortex [( 3H]-N6-(phenylisopropyl)adenosine as radioligand] or striatum [3H]-5'-(N-ethylcarbamoyl)adenosine as radioligand] for A1- and A2-adenosine receptors, respectively. Generally, 2-thio-8-cycloalkylxanthines were at least as A1 selective as the corresponding oxygen analogue. 2-Thio-8-aryl derivatives tended to be more potent at A2 receptors than the oxygen analogue. 8-[4-[(Carboxy-methyl)oxyl] phenyl]-1,3-dipropyl-2-thioxanthine ethyl ester was greater than 740-fold A1 selective.

  DOI：

  10.1021/jm00128a031
• 作为产物：
  描述：

  在 ammonium sulfide 作用下， 反应 0.25h， 以75%的产率得到1,3-di-n-propyl-5,6-diamino-2-thiouracil
  参考文献：
  名称：

  Immunosuppressive effects of 8-substituted xanthine derivatives

  摘要：

  这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。

  公开号：

  US07253176B1

文献信息

• Adenosine A1 antagonists. 3. Structure-activity relationships on amelioration against scopolamine- or N6-[(R)-phenylisopropyl]adenosine-induced cognitive disturbance
  作者：Fumio Suzuki、Junichi Shimada、Shizuo Shiozaki、Shunji Ichikawa、Akio Ishii、Joji Nakamura、Hiromi Nonaka、Hiroyuki Kobayashi、Eiichi Fuse

  DOI：10.1021/jm00069a009

  日期：1993.8

  The effects of a variety of adenosine A1 and A2 antagonists on N6-((R)-phenylisopropyl)adenosine (R-PIA)- and scopolamine-induced amnesias were investigated in rodents in order to clarify the role of adenosine receptors in learning and memory. Some of the selective adenosine A1 antagonists exhibited antiamnesic activities at several doses where they did not induce an increase of spontaneous locomotion

  在啮齿动物中研究了各种腺苷A1和A2拮抗剂对N6-（（R）-苯基异丙基）腺苷（R-PIA）-和东pol碱诱导的健忘症的作用，以阐明腺苷受体在学习和记忆中的作用。一些选择性腺苷A1拮抗剂在几种剂量下均表现出抗记忆删除功能，在这些剂量下它们不会诱导自发运动的增加。这些结果表明，在学习和记忆中，A1受体的阻断比A2受体的阻断更为重要。在两个健忘症模型中对腺苷A1拮抗剂的构效关系的详细研究表明，存在三种类型的腺苷A1拮抗剂：（A）化合物3-5（8-取代的1,3-二丙基黄嘌呤）改善了两个模型中缩短的潜伏期。（B）化合物7-11（8-取代的1，3-二烷基黄嘌呤）和19-21（咪唑并[2,1-i]嘌呤-5（4H）-一衍生物）改善了（R）-PIA引起的健忘症模型中潜伏期的缩短，但在东pol碱引起的健忘症中却没有改善。模型。（C）在东-16碱模型中化合物14-16改善了缩短的潜伏期，但在（R）-PIA模型中
• Xanthine derivatives
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05068236A1

  公开（公告）日：1991-11-26

  Novel xanthine compounds represented by the following formula: ##STR1## and pharmaceutically acceptable salts thereof have a diuretic action, a renal-protecting action and a vasodilative action. The compounds are useful as a diuretic, a renal-protecting agent and an antihypertensive agent.

  新型黄嘌呤化合物的化学式如下：##STR1##及其药用盐具有利尿作用、肾脏保护作用和扩血管作用。这些化合物可用作利尿剂、肾脏保护剂和降压药。
• A new selective preparation of ethyl 7-aminopteridine-6- carboxylate derivatives and related compound
  作者：Yoichi Yamada、Heinosuke Yasuda、Yuichi Yoshihara、Kazue Yoshizawa

  DOI：10.1002/jhet.5570360534

  日期：1999.9

  A series of ethyl 7-amino-2,4-dioxopteridine-6-carboxylates 4 and ethyl 7-amino-4-oxo-2-thioxopteridine-6-carboxylates 5, of interest biologically, has been prepared in one step from the reaction of such vicinal-diamines as 1,3-dialkyl-5,6-diaminouracils 2 or 1,3-dialkyl-5,6-diamino-2-thiouracils 3 with diethyl (E)-2,3-dicyanobutenedioate (1). Moreover, ethyl 3-amino[1,2,4]triazino[2,3-a]-1H-benzi

  在反应的一个步骤中，已制备出一系列生物学上有意义的一系列7-氨基-2,4-二氧蝶啶-6-羧酸乙酯4和7-氨基-4-氧代-2-硫代蝶啶-6-羧酸乙酯5诸如1，3-二烷基-5，6-二氨基尿嘧啶2或1，3-二烷基-5，6-二氨基-2-硫尿嘧啶3之类的邻位二胺与（E）-2，3-二氰基丁二酸二乙酯（1）。另外，通过1，2-二氨基-1H-苯并咪唑的反应，也得到了3-氨基[1,2,4]三嗪基[2,3- a ] -1H-苯并咪唑-2-羧酸乙酯（11）。（10）和1。通过nmr实验对所制备的4、5和11的结构进行了详细研究。
• [EN] POLYCYCLOALKYLPURINES AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] POLYCYCLOALKYLPURINES COMME ANTAGONISTES DU RECEPTEUR D'ADENOSINE
  申请人：BIOGEN INC

  公开号：WO2001034610A1

  公开（公告）日：2001-05-17

  The invention is based on the discovery that compounds of Formula (I) are unexpectedly highly potent and selective inhibitors of the adenosine A1 receptor. Adenosine A1 antagonists can be useful in the prevention and/or treatment of numerous diseases, including cardiac and circulatory disorders, degenerative disorders of the central nervous system, respiratory disorders, and many diseases for which diuretic treatment is suitable. In one embodiment, the invention features a compound of formula (I).

  该发明基于发现，公式（I）化合物是意外的高效、选择性的腺苷A1受体拮抗剂。腺苷A1拮抗剂可用于预防和/或治疗许多疾病，包括心脏和循环系统疾病、中枢神经系统退行性疾病、呼吸系统疾病以及许多适用于利尿治疗的疾病。在一种实施例中，该发明涉及公式（I）化合物。
• Adenosine receptor antagonists and methods of making and using the same
  申请人：Biogen, Inc.

  公开号：US20040067966A1

  公开（公告）日：2004-04-08

  The invention is based on the discovery that compounds of Formula I are unexpectedly highly potent and selective inhibitors of the adenosine A 1 receptor. Adenosine A 1 antagonists can be useful in the prevention and/or treatment of numerous diseases, including cardiac and circulatory disorders, degenerative disorders of the central nervous system, respiratory disorders, and many diseases for which diuretic treatment is suitable. In one embodiment, the invention features a compound of formula 1: 1

  该发明基于发现，公式I化合物意外地具有高效和选择性的腺苷A1受体抑制剂作用。腺苷A1拮抗剂可用于预防和/或治疗许多疾病，包括心脏和循环系统疾病、中枢神经系统退行性疾病、呼吸系统疾病以及许多适合利尿治疗的疾病。在一个实施例中，该发明涉及公式1的化合物：1。