1-(benzo[d][1,3]dioxol-5-ylmethyl)urea | 65609-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-(benzo[d][1,3]dioxol-5-ylmethyl)urea
• 英文别名: benzo[1,3]dioxol-5ylmethylurea；benzo[1,3]dioxol-5-ylmethyl-urea；N'(3,4-methylenedioxybenzyl) urea；N-(1,3-benzodioxol-5-ylmethyl)urea；1,3-benzodioxol-5-ylmethylurea
• CAS: 65609-28-1
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD05854325
• 分子量: 194.19
• InChiKey: HDXQGGUSJKXTNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.4±42.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzo[d][1,3]dioxol-5-ylmethyl)urea 在 sodium methylate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 79.5h， 生成 (2-(1-(4-methoxybenzyl)-5-((benzo[d][1,3]dioxol-6-yl)methyl)-1,4,5,6-tetrahydro-4,6-dioxo-1,3,5-triazin-2-ylamino)ethyl)guanidine
  参考文献：
  名称：

  A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists

  摘要：

  A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an average yield not exceeding 30%. 2) The Mitsunobu reaction is not involved in the new synthetic scheme avoiding the use of time and solvent consuming column chromatography. All synthesized triazinediones were preliminary pharmacologically screened in vivo for their ability to reduce the Bv8-induced thermal hyperalgesia. In this assay all compounds displayed EC50 values in the picomolar-subpicomolar range, some triazinediones containing a 4-halogen substituted benzyl group in position 5 showed the best activity. The analogues containing a 4-fluorine atom (PC-7) and a 4-bromobenzyl group (PC-25) resulted 10 times more potent than the reference PC-1 that bears a 4-ethylbenzyl group. While the 4-trifluoromethylbenzyl substituted analog (PC-27) was 100 times more potent as compared to PC1. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.030
• 作为产物：
  描述：

  potassium cyanate 、 3,4-亚甲二氧基苄胺 在 氯化铵 作用下， 以 水 为溶剂， 反应 0.25h， 以90%的产率得到1-(benzo[d][1,3]dioxol-5-ylmethyl)urea
  参考文献：
  名称：

  氯化铵促进微波辐照下单取代脲的快速合成

  摘要：

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。

  DOI：

  10.1002/ejoc.202101059

文献信息

• Synthesis and Evaluation of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones as Sodium Iodide Symporter Inhibitors
  作者：Pierre Lacotte、Celine Puente、Yves Ambroise

  DOI：10.1002/cmdc.201200417

  日期：2013.1

  The sodium iodide symporter (NIS) is responsible for the accumulation of iodide in the thyroid gland. This transport process is involved in numerous thyroid dysfunctions and is the basis for human contamination in the case of exposure to radioactive iodine species. 4‐Aryl‐3,4‐dihydropyrimidin‐2(1H)‐ones were recently discovered by high‐throughput screening as the first NIS inhibitors. Described herein

  碘化钠共转运蛋白（NIS）负责碘在甲状腺中的积累。这种运输过程涉及许多甲状腺功能障碍，是暴露于放射性碘物种时人为污染的基础。4-芳基-3,4-二氢嘧啶-2（1 H）-一种通过高通量筛选最近发现的化合物是第一种NIS抑制剂。本文描述了115个在嘧啶酮核心上五个关键位置具有结构修饰的衍生物的合成和评估。这项研究为这类新型抑制剂提供了广泛的构效关系，将为进一步开发具有体内功效和足够药代动力学特性的化合物奠定基础。另外，SAR调查提供了更有效的化合物，其表现出的IC 50为3.2的n值中号在大鼠甲状腺细胞系（FRTL5）。
• MONOSUBSTITUTED UREA DERIVATIVES AS A SELF-TANNING SUBSTANCE
  申请人：MERCK PATENT GMBH

  公开号：US20200038304A1

  公开（公告）日：2020-02-06

  The present invention relates to the use of monosubstiuted urea derivatives of the formula I as self-tanning substance, for increasing melanin synthesis, for improving melanin transport and/or improving the distribution of melanin in suprabasal layers, and to preparations comprising these urea derivatives.

  本发明涉及使用式I的单取代脲衍生物作为自日晒剂，用于增加黑色素合成，改善黑色素运输和/或改善黑色素在基底层上方的分布，以及包含这些脲衍生物的制剂。
• Synthesis of antiulcer compounds
  申请人：Janus Farmaceutici S.r.l.

  公开号：US05030738A1

  公开（公告）日：1991-07-09

  To synthesize molecules with antiulcer action, specifically ranitidine, niperotidine and cimetidine, having the formula: ##STR1## wherein R.sub.1 is hydrogen or together with R.sub.2 represents the rest of a cycloaliphatic or heterocyclic optionally substituted ring with 5 or 6 carbon atoms, R.sub.2 represents H, alkyl, alkyl substituted with a simple or substituted aromatic ring or with a single or substituted heterocyclic ring, Ar represents a simple or substituted phenyl group, a simple or substituted heterocyclic aromatic group, N=1, 2, 3, 4, 5 or 6 and X represents CH--NO.sub.2, S, N--C.tbd.N, the compound (II) is prepared through the following process sequence: ##STR2## wherein Z=H, NO.sub.2, halogen and R.sub.3 =--(CH.sub.2).sub.n Ar, --(CH.sub.2).sub.n --SH, --(CH.sub.2).sub.n --S--S--(CH.sub.2).sub.n, --(CH.sub.2).sub.n --S--CH.sub.2 Ar Y being halogen. The urea of formula ##STR3## is converted in a first stage into the corresponding carbodiimide ##STR4## by reaction with triphenylphosphine and bromine in the presence of a strong base and in a second stage is obtained the desired compound by reaction with nitromethane or with a saline derivative of cynamide.

  为合成具有抗溃疡作用的分子，具体为雷尼替丁、尼佩罗替丁和西米替丁，具有以下结构式：##STR1##其中R.sub.1为氢或与R.sub.2一起表示具有5或6个碳原子的环脂环或杂环，R.sub.2表示H、烷基、带有简单或取代芳香环的烷基或带有单个或取代杂环的烷基，Ar表示简单或取代的苯基、简单或取代的杂环芳基，N=1、2、3、4、5或6，X表示CH--NO.sub.2、S、N--C.tbd.N，化合物(II)通过以下过程序列制备：##STR2##其中Z=H、NO.sub.2、卤素，R.sub.3=--(CH.sub.2).sub.n Ar、--(CH.sub.2).sub.n --SH、--(CH.sub.2).sub.n --S--S--(CH.sub.2).sub.n、--(CH.sub.2).sub.n --S--CH.sub.2 Ar，Y为卤素。式##STR3##的脲转化为相应的碳二亚胺##STR4##在强碱存在下，通过与三苯基膦和溴的反应，在第一阶段将获得的化合物与硝基甲烷或氰胺的盐衍生物反应以获得所需的化合物。
• 3-(arylalkyl) xanthines
  申请人：Euro-Celtique S.A.

  公开号：US06248746B1

  公开（公告）日：2001-06-19

  With the above and other objects in view, the present invention comprises compounds having the general formula (I): wherein: R1 is a C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-8 cycloalkyl, C3-8 cycloalkenyl or cycloalkynyl, wherein said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or cycloalkynyl is optionally substituted with hydroxy, C1-5 alkoxy, C3-5 cycloalkoxy, halogen, oxo, carbamido, hydroxycarbamido, oximido, C1-5 alkyloximido, C3-5 cycloalkyloximido, C1-5 acyloximido or C3-5 cycloacyloximido; Q is methylene or ethylene; R3 is aryl or heteroaryl wherein said aryl or heteroaryl has one to three substituents selected from the group consisting of C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C3-6 cycloalkenyl, cycloalkynyl, C3-5 alkylene, C3-5 cycloalkylene, haloC1-6 alkyl, haloC1-6 cycloalkyl, hydroxy, C1-5 alkoxy, C3-5 cycloalkoxy, C1-2 alkylenedioxy, C1-6 acyl, C3-6 cycloacyl, C1-6 acyloxy, C3-6 cycloacyloxy, halogen, nitro or cyano; R8 is C1-5 alkyl or C3-5 cycloalkyl, optionally substituted by hydroxy, C1-5 alkyloxy, C3-5 cycloalkyloxy, C1-5 acyloxy, C3-5 cycloacyloxy or halogen; and methods of using the compounds of formula I for treatment of patients who can benefit from a modification of PDE IV levels in their bodies.

  考虑到上述和其他目的，本发明涉及具有通式（I）的化合物：其中：R1是C2-8烷基，C2-8烯基，C2-8炔基，C3-8环烷基，C3-8环烯基或环炔基，其中所述烷基，烯基，炔基，环烷基，环烯基或环炔基可以选择性地用羟基，C1-5烷氧基，C3-5环烷氧基，卤素，氧代，氨基甲酰基，羟基氨基甲酰基，肟基，C1-5烷氧肟基，C3-5环烷氧肟基，C1-5酰氧肟基或C3-5环酰氧肟基取代；Q是亚甲基或乙烯基；R3是芳基或杂芳基，其中所述芳基或杂芳基具有1-3个取自C1-6烷基，C2-6烯基，C2-6炔基，C3-6环烷基，C3-6环烯基，环炔基，C3-5烷基，C3-5环烷基，卤代C1-6烷基，卤代C1-6环烷基，羟基，C1-5烷氧基，C3-5环烷氧基，C1-2烷二氧基，C1-6酰基，C3-6环酰基，C1-6酰氧基，C3-6环酰氧基，卤素，硝基或氰基的取代基；R8是C1-5烷基或C3-5环烷基，可以选择性地被羟基，C1-5烷氧基，C3-5环烷氧基，C1-5酰氧基，C3-5环酰氧基或卤素取代；以及使用式I化合物治疗需要改变其体内PDE IV水平的患者的方法。
• Monosubstituted urea derivatives as a self-tanning substance
  申请人：MERCK PATENT GMBH

  公开号：US11234914B2

  公开（公告）日：2022-02-01

  The present invention relates to the use of monosubstiuted urea derivatives of the formula I as self-tanning substance, for increasing melanin synthesis, for improving melanin transport and/or improving the distribution of melanin in suprabasal layers, and to preparations comprising these urea derivatives.

  本发明涉及将式 I 的单取代脲衍生物用作自鞣物质，以增加黑色素的合成，改善黑色素的运输和/或改善黑色素在基底层上的分布，还涉及包含这些脲衍生物的制剂。