N-苯并[1,3]二氧五环-5-基-2-氯乙酰胺 | 227199-07-7

• 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
• 中文名称: N-苯并[1,3]二氧五环-5-基-2-氯乙酰胺
• 中文别名: N-1,3-苯并二氧代l-5-基-2-氯乙酰胺
• 英文名称: α-chloro-N-(3,4-methylenedioxyphenyl)acetamide
• 英文别名: N-(benzo[d](1,3)dioxol-5-yl)-2-chloroacetamide；N-(benzo[d][1,3]dioxol-5-yl)-2-chloroacetamide；N-benzo[1,3]dioxol-5-yl-2-chloroacetamide；N-1,3-benzodioxol-5-yl-2-chloroacetamide；chloro-acetic acid benzo[1,3]dioxol-5-ylamide；Chlor-essigsaeure-benzo[1,3]dioxol-5-ylamid；N-(1,3-benzodioxol-5-yl)-2-chloroacetamide
• CAS: 227199-07-7
• 化学式: C₉H₈ClNO₃
• mdl: MFCD00245737
• 分子量: 213.62
• InChiKey: HBIYZYYNHWRQMC-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156
• 沸点：
  399.5±42.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2932999099
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H315,H318,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  N-苯并[1,3]二氧五环-5-基-2-氯乙酰胺 在 palladium on activated charcoal sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 2-(4-aminophenoxy)-N-benzo[1,3]dioxol-5-ylacetamide
  参考文献：
  名称：

  N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

  摘要：

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.055
• 作为产物：
  描述：

  3,4-亚甲二氧基苯胺 以92%的产率得到N-苯并[1,3]二氧五环-5-基-2-氯乙酰胺
  参考文献：
  名称：

  Acetamides and benzamides that are useful in treating sexual dysfunction

  摘要：

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。

  公开号：

  US20040029887A1

文献信息

• Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and Stimulator for Interferon Genes (STING) modulators as cancer immunotherapeutics
  申请人：Stingray Therapeutics, Inc.

  公开号：US20200039979A1

  公开（公告）日：2020-02-06

  Substituted -3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and related compounds, which are useful as inhibitors of ENPP1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the ENPP1.

  取代的-3H-咪唑[4,5-c]吡啶和1H-吡咯[2,3-c]吡啶系列新型胞外核苷酸焦磷酸酶/磷酸二酯酶-1 (ENPP1)及相关化合物，其作为ENPP1的抑制剂是有用的；制造这些化合物的方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与ENPP1功能障碍相关的疾病的方法。
• CONJUGATED PROTEINS AND USES THEREOF
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20200278355A1

  公开（公告）日：2020-09-03

  Disclosed herein, in certain embodiments, are protein-probe adducts and synthetic ligands that inhibit protein-probe adduct formation, in which the proteins are regulated by NRF2. In some instances, also described herein are protein-binding domains that interact with a probe and/or a ligand described herein, in which the proteins are regulated by NRF2.

  在某些实施例中，本文披露了蛋白质探针加合物和合成配体，可以抑制蛋白质探针加合物的形成，其中这些蛋白质受NRF2调控。在某些情况下，本文还描述了与本文描述的探针和/或配体相互作用的蛋白结合结构域，其中这些蛋白质受NRF2调控。
• Highly Potent and Selective Butyrylcholinesterase Inhibitors for Cognitive Improvement and Neuroprotection
  作者：Qi Li、Ying Chen、Shuaishuai Xing、Qinghong Liao、Baichen Xiong、Yuanyuan Wang、Weixuan Lu、Siyu He、Feng Feng、Wenyuan Liu、Yao Chen、Haopeng Sun

  DOI：10.1021/acs.jmedchem.1c00167

  日期：2021.5.27

  Butyrylcholinesterase (BChE) has been considered as a potential therapeutic target for Alzheimer’s disease (AD) because of its compensation capacity to hydrolyze acetylcholine (ACh) and its close association with Aβ deposit. Here, we identified S06-1011 (hBChE IC50 = 16 nM) and S06-1031 (hBChE IC50 = 25 nM) as highly effective and selective BChE inhibitors, which were proved to be safe and long-acting

  丁酰胆碱酯酶（BChE）因其水解乙酰胆碱（ACh）的补偿能力及其与Aβ沉积的密切关系而被认为是阿尔茨海默病（AD）的潜在治疗靶点。在这里，我们确定了S06-1011 ( h BChE IC 50 = 16 nM) 和S06-1031 ( h BChE IC 50 = 25 nM) 为高效、选择性 BChE 抑制剂，并被证明是安全且长效的。候选化合物在东莨菪碱和 Aβ 1-42肽诱导的认知缺陷模型中表现出神经保护作用和改善认知的能力。最佳候选者S06-1011提高了BChE底物ghrelin的水平，可以起到改善精神情绪食欲的作用。 S06-1011处理组的体重增加显着增加。因此，抑制BChE不仅对痴呆具有保护作用，而且对治疗和护理也有很大作用。
• Synthesis of annulated heterocyclic systems based on 4-CF3- or 4-CHF2-3-cyano-(1H)-pyridine-2-thiones
  作者：L. A. Rodinovskaya、A. E. Fedorov、A. M. Shestopalov、P. A. Belyakov、K. G. Nikishin

  DOI：10.1007/s11172-013-0321-9

  日期：2013.10

  A simple and convenient preparative method for the synthesis of 3-cyano-4-difluoro- and -trifluoromethylpyridine-2(1H)-thiones was developed. During studies of synthetic potential of these compounds, approaches to the synthesis of a number of annulated heterocyclic systems were suggested.

  开发了一种简便的合成方法，用于合成3-氰基-4-二氟和-三氟甲基吡啶-2(1H)-硫醇。在研究这些化合物的合成潜力过程中，提出了一系列环合杂环体系的合成方法。
• Structure-based Design, Synthesis, and Biological Evaluation of Isatin Derivatives as Potential Glycosyltransferase Inhibitors
  作者：Yong Wang、Fung-Yi Chan、Ning Sun、Hok-Kiu Lui、Pui-Kin So、Siu-Cheong Yan、Kin-Fai Chan、Jiachi Chiou、Sheng Chen、Ruben Abagyan、Yun-Chung Leung、Kwok-Yin Wong

  DOI：10.1111/cbdd.12361

  日期：2014.12

  biosynthesis. Structure‐based virtual screening of about 3 000 000 commercially available compounds against the crystal structure of the glycosyltransferase (GT) domain of the Staphylococcus aureus penicillin‐binding protein 2 (S. aureus PBP2) resulted in identification of an isatin derivative, 2‐(3‐(2‐carbamimidoylhydrazono)‐2‐oxoindolin‐1‐yl)‐N‐(m‐tolyl)acetamide (4) as a novel potential GT inhibitor. A series

  肽聚糖糖基转移酶（PGT）已被证明是抑制细菌细胞壁生物合成的重要药理靶标。对金黄色葡萄球菌青霉素结合蛋白2（金黄色葡萄球菌PBP2）的糖基转移酶（GT）结构域的晶体结构进行约3,000万市售化合物的基于结构的虚拟筛选，结果发现了靛红衍生物2-（ 3-（2-氨基甲酰肼基）-2-氧吲哚-1-基）-N-（间甲苯基）乙酰胺（4）作为潜在的新型GT抑制剂。合成了一系列的4种衍生物。几种化合物显示出比初始命中化合物更有效的抗菌活性4，尤其是2-（3-（2-氨基甲酰肼基）-2-氧吲哚-1-基）-N-（3-硝基苯基）乙酰胺（4l），对革兰氏阳性枯草芽孢杆菌和金黄色葡萄球菌的MIC值为24和 48μg / mL。饱和转移差异（STD）NMR研究表明，在4l和金黄色葡萄球菌PBP2的GT结构域之间存在结合接触。竞争性STD-NMR进一步证明了4l和Moenomycin A以竞争性方式与GT结构域结合。分子对接