(+/-)-5,6,7,8-tetrahydro-2,6-quinazolinediamine | 285139-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+/-)-5,6,7,8-tetrahydro-2,6-quinazolinediamine
• 英文别名: 5,6,7,8-Tetrahydroquinazoline-2,6-diamine
• CAS: 285139-05-1
• 化学式: C₈H₁₂N₄
• mdl: MFCD08447441
• 分子量: 164.21
• InChiKey: KXBJGRDEMICURJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-5,6,7,8-tetrahydro-2,6-quinazolinediamine 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.75h， 生成 methyl 3-((6-(1H-indole-2-carboxamido)-5,6,7,8-tetrahydroquinazolin-2-yl)amino)-3-oxopropanoate
  参考文献：
  名称：

  Discovery of 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site

  摘要：

  Bacterial DNA gyrase and topoisomerase IV are essential enzymes that control the topological state of DNA during replication and validated antibacterial drug targets. Starting from a library of marine alkaloid oroidin analogues, we identified low micromolar inhibitors of Escherichia coil DNA gyrase based on the 5,6,7,8-tetrahydroquinazoline and 4,5,6,7-tetrahydrobenzo [1,2-d]thiazole scaffolds. Structure-based optimization of the initial hits resulted in low nanomolar E. coil DNA gyrase inhibitors, some of which exhibited micromolar inhibition of E. coil topoisomerase IV and of Staphylococcus aureus homologues. Some of the compounds possessed modest antibacterial activity against Gram positive bacterial strains, while their evaluation against wild-type, impA and Delta tolC E. coil strains suggests that they are efflux pump substrates and/or do not possess the physicochemical properties necessary for cell wall penetration. Our study provides a rationale for optimization of this class of compounds toward balanced dual DNA gyrase and topoisomerase IV inhibitors with antibacterial activity.

  DOI：

  10.1021/acs.jmedchem.5b00489
• 作为产物：
  描述：

  trans-4-Aminocyclohexanol 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 sodium ethanolate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 42.5h， 生成 (+/-)-5,6,7,8-tetrahydro-2,6-quinazolinediamine
  参考文献：
  名称：

  2-氨基-7,8-二氢-6（5 H）-喹唑啉酮，2,4-二氨基-7,8-二氢-6（5 H）-喹唑啉酮，5,6,7,8-四氢- 2,6-喹唑啉二胺和5,6,7,8-四氢-2,4,6-喹唑啉三胺衍生物

  摘要：

  N-（2-氨基-5,6,7,8-四氢-6-喹唑啉基）乙酰胺（9）和N-（2,4-二氨基-5,6,7,8-四氢-6-喹唑啉基）乙酰胺（6）由N-（4-氧代环己基）乙酰胺（5）合成，作为新型拟肽构筑物。具有相似目的的N-（6-氧代-5,6,7,8-四氢-2-喹唑啉基）乙酰胺（18）和N- [2-（乙酰氨基）-6-氧代-5,6,7,8由环己烷-1，4-二酮单亚乙基缩酮（11）制备-四氢-4-喹唑啉基]乙酰胺（14）。

  DOI：

  10.1002/jhet.5570370229

文献信息

• Methods for synthesizing organoboronic compounds and products thereof
  申请人：Walter Armin

  公开号：US20050119226A1

  公开（公告）日：2005-06-02

  Organoboronic acids, for example Cbz-(R)-Phe-(S)-Pro-(R)-Mpg-B(OH) 2 , are made by hydrolysing their diethanolamine adducts under conditions which avoid substantial C—B bond breakage. The product acids are substantially free of degradation product derived from cleavage of the C—B bond thereof. The acids are used to make base addition salts thereof. The salts are formulated into anti-thrombotic pharmaceutical formulations.

  有机硼酸，例如Cbz-(R)-Phe-(S)-Pro-(R)-Mpg-B(OH)2，是通过在避免大量C—B键断裂的条件下水解它们的二乙醇胺加合物制备的。所得的产物酸基本上不含有从C—B键裂解产生的降解产物。这些酸用于制备它们的碱盐。这些盐被配制成抗血栓药物配方。
• Substituted 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2-yl compounds and 5,6,7,8-tetrahydroquinazoline-2-yl compounds
  申请人：Oberboersch Stefan

  公开号：US20070249631A1

  公开（公告）日：2007-10-25

  Substituted 5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl and 5,6,7,8-tetrahydro-quinazolin-2-yl compounds, corresponding to formula I processes for the production thereof, pharmaceutical preparations containing these compounds the use thereof for the production of pharmaceutical preparations and related method of treating or inhibiting certain disorders or conditions, including pain.

  将5,6,7,8-四氢吡啶并[4,3-d]嘧啶-2-基和5,6,7,8-四氢喹唑啉-2-基化合物替代为公式I，生产这些化合物的方法，含有这些化合物的药物制剂，以及利用它们生产药物制剂和相关方法治疗或抑制某些疾病或症状，包括疼痛。
• Thrombin inhibitors
  申请人：——

  公开号：US20030191139A1

  公开（公告）日：2003-10-09

  The invention relates to compounds of formula I D—CO—B—A-Het and pharmaceutically acceptable salts thereof where substituents in description have the specified meanings. The compounds are used as thrombin inhibitors.

  该发明涉及公式I的化合物D—CO—B—A-Het及其药用可接受的盐，其中描述中的取代基具有指定的含义。这些化合物被用作凝血酶抑制剂。
• Peptide boronic acids useful in making salts thereof
  申请人：Madge Jonathan David

  公开号：US20050176651A1

  公开（公告）日：2005-08-11

  Tripeptide boronic acids of (R,S,R) configuration, for example Cbz-(R)-Phe-(S)-Pro-(R)-Mpg-B(OH) 2 , and their use to make base addition salts of such acids. The salts are formulated into anti-thrombotic pharmaceutical formulations.

  (R,S,R)构型的三肽硼酸，例如Cbz-(R)-Phe-(S)-Pro-(R)-Mpg-B(OH)2，用于制备这种酸的碱加成盐。这些盐被配制成抗血栓药物制剂。
• Peptide boronic acid compounds useful in anticoagulation
  申请人：Combe-Marzelle Marie Sophie

  公开号：US20050282757A1

  公开（公告）日：2005-12-22

  A method for preventing thrombosis in a setting where rapid onset and/or rapid offset of anticoagulation is required, comprising administering a compound selected from the group consisting of boronic acids which have a neutral thrombin P1 domain linked to a hydrophobic moiety capable of binding to the thrombin S2 and S3 subsites, and pharmaceutically acceptable salts, prodrugs and pharmaceutically acceptable prodrug salts of such acids.

  一种用于在需要快速发生和/或快速停止抗凝的情况下预防血栓形成的方法，包括给予从羟基烷基部位能够结合凝血酶S2和S3亚位点的中性凝血酶P1结构域的硼酸化合物中选择的化合物，以及这些酸的药学上可接受的盐、前药和药学上可接受的前药盐。