2-[(3-chloropropyl)sulfanyl]-1,3-benzoxazole | 1156590-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-[(3-chloropropyl)sulfanyl]-1,3-benzoxazole
• 英文别名: 2-[(3-chloropropyl)thio]benzoxazole；2-((3-Chloropropyl)thio)benzo[d]oxazole；2-(3-chloropropylsulfanyl)-1,3-benzoxazole
• CAS: 1156590-55-4
• 化学式: C₁₀H₁₀ClNOS
• mdl: MFCD12172134
• 分子量: 227.714
• InChiKey: RSBXXWSJTZDBHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  345.7±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  咪唑 、 2-[(3-chloropropyl)sulfanyl]-1,3-benzoxazole 在 四丁基溴化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 90.0 ℃ 、1.03 MPa 条件下， 以22%的产率得到2-[[3-(1H-imidazol-1-yl)propyl]thio]benzoxazole
  参考文献：
  名称：

  Novel imidazole derivatives as heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity in human-derived cancer cell lines

  摘要：

  Heme oxygenase (HO) is a cytoprotective enzyme that can be overexpressed in some pathological conditions, including certain cancers. In this work, novel imidazole derivatives were designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2). In these compounds the imidazole ring, crucial for the activity, is connected to a hydrophobic group, represented by aryloxy, benzothiazole, or benzoxazole moieties, by means of alkyl or thioalkyl chains of different length. Many of the tested compounds were potent and/or selective against one of the two isoforms of HO. Furthermore, most of the pentyl derivatives showed to be better inhibitors of HO-2 with respect to HO-1, revealing a critical role of the alkyl chain in discriminating between the two isoenzymes. Compounds which showed the better profile of HO inhibition were selected and tested to evaluate their cytotoxic properties in prostate and breast cancer cell lines (DU-145, PC3, LnCap, MDA-MB-231, and MCF-7). In these assays, aryloxyalkyl derivatives resulted more cytotoxic than benzothiazolethioalkyl ones; in particular compound 31 was active against all the cell lines tested, confirming the anti-proliferative properties of HO inhibitors and their potential use in the treatment of specific cancers. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.003
• 作为产物：
  描述：

  1-溴-3-氯丙烷 、 2-巯基苯并恶唑 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以67%的产率得到2-[(3-chloropropyl)sulfanyl]-1,3-benzoxazole
  参考文献：
  名称：

  新型4-苯胺基喹唑啉衍生物的合成及体外抗肿瘤活性

  摘要：

  设计了一系列6，7-二烷氧基-4-苯胺基喹唑啉，通过在喹唑啉的6-位取代不同的杂环和在4-位取代多种苯胺来合成。通过使用非过度表达的肿瘤细胞作为阴性对照（乳腺癌细胞系MCF-7），筛选了这些新型喹唑啉化合物对过表达表皮生长因子受体的皮肤表皮样癌细胞系（A431）的细胞毒性作用。2-丁基-4-氯-1- {3- [7-甲氧基-4-（3-（三氟甲基）苯基氨基）喹唑啉-6-酰氧基]-丙基} -1 H-咪唑-5-甲醛（30）和2-丁基-4-氯-1- {3- [4-（3-碘苯基氨基）-7-甲氧基喹唑啉-6-酰氧基]丙基} -1 H-咪唑-5-甲醛（33）被发现对A431细胞系（IC 50 3.5和3μM）更有效，其活性与吉非替尼相当。使用人EGFR酪氨酸激酶结构域（PDB id-2gs2）进行的计算机对接实验表明，与吉非替尼的33个对接在同一位置，涉及Val702，Ala719，Ser696和Lys721。

  DOI：

  10.1016/j.ejmech.2008.07.023

文献信息

• Synthesis of novel tetrazole derivatives and evaluation of their antifungal activity
  作者：Edyta Łukowska-Chojnacka、Jolanta Mierzejewska、Małgorzata Milner-Krawczyk、Małgorzata Bondaryk、Monika Staniszewska

  DOI：10.1016/j.bmc.2016.09.066

  日期：2016.11

  With the appearance of the antifungal resistance, novel antifungal agents need to be identified. In this context new 2,5-disubstituted tetrazole derivatives containing benzothiazole, benzoxazole or phenylsulfonyl moiety were synthesized by N-alkylation of aryltetrazole with 2-[(3-chloropropyl)sulfanyl]-1,3-benzothiazole or 2-[(3-chloropropyl)sulfanyl]-1,3-benzoxazole and Michael-type addition of aryltetrazole

  随着抗真菌剂的出现，需要鉴定新型抗真菌剂。在这种情况下，通过用2-[（（3-氯丙基）硫烷基] -1,3-苯并噻唑或2-[（（3-氯丙基）硫烷基] -1,3-苯并恶唑和芳基四唑的迈克尔型加成到苯基乙烯基砜中。借助于1H NMR，13C NMR，IR和HRMS光谱数据确认了合成化合物的化学结构。测试了以下化合物对霉菌的影响：镰孢镰刀菌，尖孢镰刀菌，炭疽菌，黑曲霉和酵母白色念珠菌。结果表明，在模具中，只有C. coccodes对所有检查的结构都非常敏感。所有四唑衍生物均以相同的水平对抗白色念珠菌，并在16至0.0313μg/ mL的浓度范围内表现出较高的细胞生长抑制作用（97-99％）。2-（3- [5-（4-氯苯基）-2H-四唑-2-基]丙基}硫烷基）-1,3-苯并恶唑（5c）和2-（3- [5 -（2-氯苯基）-2H-四唑-2-基]丙基}硫烷基）-1,3-苯并恶唑（5d）是通过在渗透保护
• Benzimidazolidinone derivatives as muscarinic agents
  申请人：Kelly Michael Nicholas

  公开号：US20060199799A1

  公开（公告）日：2006-09-07

  Benzimidazolidinone derivative compounds, which increase acetylcholine signaling or effect in the brain, and highly selective muscarinic agonists, particularly for the M 1 and/or M 4 receptor subtypes, pharmaceutical compositions comprising the same, as well as methods of treating psychosis using these compounds are disclosed.

  苯并咪唑烷酮衍生物化合物可增加乙酰胆碱在大脑中的信号传递或作用，同时也是高选择性毒蕈碱激动剂，尤其是对 M 1 和/或 M 4 公开了包含这些化合物的药物组合物以及使用这些化合物治疗精神病的方法。
• BENZIMIDAZOLIDINONE DERIVATIVES AS MUSCARINIC AGENTS
  申请人：Kelly Michael Nicholas

  公开号：US20080009520A1

  公开（公告）日：2008-01-10

  Benzimidazolidinone derivative compounds, which increase acetylcholine signaling or effect in the brain, and highly selective muscarinic agonists, particularly for the M 1 and/or M 4 receptor subtypes, pharmaceutical compositions comprising the same, as well as methods of treating psychosis using these compounds are disclosed.
• US7273857B2
  申请人：——

  公开号：US7273857B2

  公开（公告）日：2007-09-25
• US7291611B2
  申请人：——

  公开号：US7291611B2

  公开（公告）日：2007-11-06