1-异氰酸基-3-甲氧基丙烷 | 7019-13-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-异氰酸基-3-甲氧基丙烷
• 中文别名: 1-异氰酸-3-甲氧基丙烷
• 英文名称: 3-Methoxy-propylisocyanat
• 英文别名: 1-Isocyanato-3-methoxypropane
• CAS: 7019-13-8
• 化学式: C₅H₉NO₂
• mdl: MFCD09901269
• 分子量: 115.132
• InChiKey: IQOIAHPAAZJVOX-UHFFFAOYSA-N

物化性质

• 沸点：
  102 °C(Press: 186 Torr)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2929109000

反应信息

• 作为反应物：
  描述：

  1-异氰酸基-3-甲氧基丙烷 、 金刚烷胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到1-(1-adamantyl)-3-(3-methoxypropyl)urea
  参考文献：
  名称：

  The structure–activity relationship of urea derivatives as anti-tuberculosis agents

  摘要：

  The treatment of tuberculosis is becoming more difficult due to the ever increasing prevalence of drug resistance. Thus, it is imperative that novel anti-tuberculosis agents, with unique mechanisms of action, be discovered and developed. The direct anti-tubercular testing of a small compound library led to discovery of adamantyl urea hit compound 1. In this study, the hit was followed up through the synthesis of an optimization library. This library was generated by systematically replacing each section of the molecule with a similar moiety until a clear structure-activity relationship was obtained with respect to antitubercular activity. The best compounds in this series contained a 1-adamantyl-3-phenyl urea core and had potent activity against Mycobacterium tuberculosis plus an acceptable therapeutic index. It was noted that the compounds identified and the pharmacophore developed is consistent with inhibitors of epoxide hydrolase family of enzymes. Consequently, the compounds were tested for inhibition of representative epoxide hydrolases: M. tuberculosis EphB and EphE; and human soluble epoxide hydrolase. Many of the optimized inhibitors showed both potent EphB and EphE inhibition suggesting the antitubercular activity is through inhibition of multiple epoxide hydrolase enzymes. The inhibitors also showed potent inhibition of humans soluble epoxide hydrolase, but limited cytotoxicity suggesting that future studies must be towards increasing the selectivity of epoxide hydrolase inhibition towards the M. tuberculosis enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.034
• 作为产物：
  描述：

  (E)-2-(hydroxyimino)-N-(3-methoxypropyl)propanamide 在 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-异氰酸基-3-甲氧基丙烷
  参考文献：
  名称：

  丙酮酸甲酯肟作为羰基合成子：脲、氨基甲酸酯、硫代氨基甲酸酯和苯胺的合成

  摘要：

  以丙酮酸甲酯肟为羰基合成子，开发了合成不对称脲、氨基甲酸酯、硫代氨基甲酸酯和苯胺的新策略。该试剂的固有反应性使得能够进行连续的取代，包括直接酰胺化和用各种亲核试剂进行一锅脱肟取代。该方法的实用性通过生物活性分子的合成得到了证明。

  DOI：

  10.1021/acs.orglett.4c01007

文献信息

• Catalytic Asymmetric Synthesis of Diketopiperazines by Intramolecular Tsuji–Trost Allylation
  作者：Matteo Faltracco、Silvia Cotogno、Christophe M. L. Vande Velde、Eelco Ruijter

  DOI：10.1021/acs.joc.9b01994

  日期：2019.9.20

  We report the intramolecular Tsuji–Trost reaction of Ugi adducts to give spiro-diketopiperazines in high yield and with high enantioselectivity. This approach allows the catalytic asymmetric construction of a broad range of these medicinally important heterocycles under mild conditions, in two steps from cheap, commercially available starting materials.

  我们报道了Ugi加合物的分子内Tsuji-Trost反应，以高产率和高对映选择性提供了螺-二酮哌嗪。这种方法允许在温和条件下分两步从廉价的市售起始原料中催化广泛地合成这些医学上重要的杂环。
• Development of Chiral <i>N</i>-Alkylcarbamates as New Leads for Potent and Selective H₃-Receptor Antagonists:  Synthesis, Capillary Electrophoresis, and in Vitro and Oral in Vivo Activity
  作者：Astrid Sasse、Katarzyna Kiec-Kononowicz、Holger Stark、Malgorzata Motyl、Sibylle Reidemeister、C. Robin Ganellin、Xavier Ligneau、Jean-Charles Schwartz、Walter Schunack

  DOI：10.1021/jm9804376

  日期：1999.2.1

  N-2-heptylcarbamate showed a stereoselective differentiation in their pharmacological effect in vivo (ED50 of 0.39 mg/kg for the (S)-derivative vs 1.5 mg/kg for the (R)-derivative) most probably caused by differences in pharmacokinetic parameters. H1- and H2-receptor activities were determined for some of the novel carbamates, demonstrating that they have a highly selective action at the histamine H3 receptor

  制备具有N-烷基链的作为3-（1H-咪唑-4-基）丙醇的衍生物的新型氨基甲酸酯作为组胺H3-受体拮抗剂。N-烷基侧链与甲基的分支产生手性化合物，其通过Mitsunobu方案改编的Gabriel合成立体定向地合成。通过毛细管电泳（CE）测定某些手性化合物的光学纯度（ee> 95％）。在大鼠大脑皮层突触体上的组胺H3受体功能测试中，所研究的化合物显示出明显的高拮抗剂活性（Ki值为4.1-316 nM）。在豚鼠回肠的外周模型中观察到类似的H3受体拮抗剂活性。通过体外测定未发现手性拮抗剂的H3受体的立体选择性鉴别。口服给药后，还在小鼠体内筛选所有化合物的中心H3受体拮抗剂活性。大多数化合物是H3受体介导的脑Ntau-甲基组胺水平增强的有效剂。N-2-庚基氨基甲酸酯的对映异构体在体内药理作用中表现出立体选择性差异（（S）衍生物的ED50为0.39 mg / kg，而（R）衍生物的ED50为1.5 mg
• [EN] SMALL MOLECULE ANTAGONISTS OF PF4<br/>[FR] ANTAGONISTES À PETITES MOLÉCULES DE PF4
  申请人：NEW YORK BLOOD CENTER INC

  公开号：WO2022073003A1

  公开（公告）日：2022-04-07

  The present application provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof, wherein Y, R1, R2, R3and R4are described herein. The methods of using these compounds to inhibit tetramerization of PF4 and to treat the associated diseases and conditions, such as heparin-induced thrombocytopenia and thrombosis (HITT) and vaccine-induced immune thrombotic thrombocytopenia (VITT), methods of making these compounds, and pharmaceutical compositions containing these compounds are also disclosed.

  本申请提供了式（I）的化合物或其药学上可接受的盐，其中Y，R1，R2，R3和R4如本文所述。还公开了使用这些化合物抑制PF4四聚体化和治疗相关疾病和状况的方法，例如肝素诱导的血小板减少和血栓形成（HITT）和疫苗诱导的免疫性血栓性血小板减少症（VITT），制备这些化合物的方法以及含有这些化合物的制药组合物。
• A1 adenosine receptor antagonists
  申请人：Wilson Neely Constance

  公开号：US20050119258A1

  公开（公告）日：2005-06-02

  Compounds of the general formula (I) are described: wherein A is a 5- or 6-membered aromatic or heteroaromatic ring. Compositions comprising such compounds and methods of use thereof are also described.

  描述了一般式（I）的化合物：其中A是一个5或6成员的芳香族或杂环芳香族环。还描述了包含这些化合物的组合物和使用它们的方法。
• A1 ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Wilson N. Constance

  公开号：US20070282105A1

  公开（公告）日：2007-12-06

  wherein R 3 is Alk 14 ArR 16 , and wherein Alk 14 is C 1-8 straight or branched alkylene or alkenylene. The present invention provides novel adenosine receptor antagonists, more particularly, A 1 adenosine receptor antagonists of formula (I). Pharmaceutical compositions comprising an A 1 adenosine receptor antagonist of formula (I) and a pharmaceutically acceptable carrier are further provided. Compositions also include diagnostic assay-type probes comprising a novel A 1 adenosine receptor antagonist of formula (I) that is labeled or conjugated with radioactive or non-radioactive material. Methods for treating A 1 adenosine receptor related disorders comprising administering an A 1 adenosine receptor antagonist of formula (I) are also disclosed. The novel A 1 adenosine receptor antagonist compositions of formula (I) find further use in diagnostic and imaging methods.

  本发明提供了一种新型的腺苷受体拮抗剂，更具体地说，是式（I）的A1腺苷受体拮抗剂，其中R3为Alk14ArR16，Alk14为C1-8直链或支链烷基或烯基。还提供了包含式（I）的A1腺苷受体拮抗剂及其药用载体的制药组合物。组合物还包括诊断性检测探针，其中包含一种新型的标记或与放射性或非放射性物质结合的式（I）的A1腺苷受体拮抗剂。还揭示了通过给予式（I）的A1腺苷受体拮抗剂治疗A1腺苷受体相关疾病的方法。式（I）的新型A1腺苷受体拮抗剂组合物在诊断和成像方法中找到了进一步的应用。