6-(2-iodophenyl)hex-5-yn-1-ol | 151860-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2-iodophenyl)hex-5-yn-1-ol
• CAS: 151860-00-3
• 化学式: C₁₂H₁₃IO
• 分子量: 300.139
• InChiKey: NKNXUYDKUCAJPO-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±27.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(2-iodophenyl)hex-5-yn-1-ol 在 copper(l) iodide 、 四(三苯基膦)钯 、 Celite 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成
  参考文献：
  名称：

  Synthetic studies of the tandem enediyne-mono- and bisradical cyclizations

  摘要：

  The readily synthesized enediynes 12a-j possessing a tethered olefin radical acceptor can participate in a tandem enediyne-radical cyclization to yield dibydrobenzindene derivatives 14a-j. In the present study, the scope of this reaction was expanded to include a wide variety of olefin acceptors. Substitution at both ends of olefin leads to the formation of two diastereomers 14b and 14c in a 3.5:1 ratio when R3 is Me and R2 is CO2Me. The structures of the dihydrobenzindene products 14b and 14c were confirmed by generating a radical from 25 by a tributyltin hydride reaction which undergoes radical cyclization; this radical is similar to the enediyne-generated radical, which also cyclizes. It was shown that, in 14i and 14j, a substituent at R1 slowed the reaction but still resulted in a good to excellent yield of product. A tandem enediyne-6-exo-radical cyclization of 16 was also carried out but did not work as well as its 5-exo counterpart 12a. Finally, an enediyne 33 containing two olefinic tethers was cyclized in a process to form tetracycle 34 where three rings were formed in one synthetic operation.

  DOI：

  10.1021/ja00078a013
• 作为产物：
  描述：

  5-己炔-1-醇 、 1,2-二碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 反应 12.0h， 以50%的产率得到6-(2-iodophenyl)hex-5-yn-1-ol
  参考文献：
  名称：

  开发强大的17（R），18（S）-环氧二十碳四烯酸（17,18-EEQ）类似物作为潜在的临床抗心律不齐药物。

  摘要：

  17（R），18（S）-环氧二十碳四烯酸（EEQ）是二十碳五烯酸（EPA）的细胞色素P450代谢产物，是新生鼠心肌细胞（NRCM）心律不齐模型中具有低纳摩尔活性的强负性变倍体。先前的研究确定草酰胺2b是一种稳定的可溶性环氧水解酶（sEH）替代品，但由于口服生物利用度和代谢稳定性有限，因此不适合用于体内应用。这些ADME局限性已通过改善负负变时剂（例如4和16）的产生得到解决，这些负变时剂被评估为潜在的临床候选药物。

  DOI：

  10.1021/acs.jmedchem.9b00952

文献信息

• [EN] NOVEL CYP-EICOSANOID DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS CYP-ÉICOSANOÏDE
  申请人：MAX DELBRÜCK CT FÜR MOLEKULARE MEDIZIN

  公开号：WO2015110262A1

  公开（公告）日：2015-07-30

  The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.

  本发明涉及一般式（I）的化合物，这些化合物是由细胞色素P450（CYP）酶从ω-3（n-3）多不饱和脂肪酸（PUFAs）产生的环氧代谢产物的类似物。本发明还涉及含有这些化合物中的一个或多个的组合物，以及利用这些化合物或组合物治疗或预防与炎症、增殖、高血压、凝血、免疫功能、病理性血管生成、心力衰竭和心律失常相关的疾病和症状。
• Enediynes bearing polyfluoroaryl sulfoxide as new antiproliferative agents with dual targeting of microtubules and DNA
  作者：Cyril Borie、Shovan Mondal、Tanzeel Arif、Manon Briand、Hugo Lingua、Frédéric Dumur、Didier Gigmes、Pierre Stocker、Bernadette Barbarat、Viviane Robert、Cendrine Nicoletti、Daniel Olive、Marc Maresca、Malek Nechab

  DOI：10.1016/j.ejmech.2018.02.030

  日期：2018.3

  A novel series of enediynes possessing pentafluorophenylsulfoxide have been developed. The innovative compounds possess antiproliferative activity against a broad panel of human cancer cells originating from breast, blood, lung, kidney, colon, prostate, pancreas or skin with IC50 ranging from 0.6 to 3.4 μM. The antiproliferative activity of enediynes in darkness is associated to their ability to compromise

  已经开发了具有五氟苯基亚砜的一系列新的烯二炔。该创新化合物具有抗增殖活性，可对抗源自乳腺癌，血液，肺，肾，结肠，前列腺，胰腺或皮肤的多种人类癌细胞，IC 50范围为0.6至3.4μM。烯二炔在黑暗中的抗增殖活性与其破坏微管网络的能力有关。此外，暴露于紫外线会导致由新合成的分子引起的双链DNA裂解，从而进一步降低了其IC 50纳摩尔级的抗人肿瘤细胞，包括抗化学性的胰腺癌细胞。综上所述，检查的数据表明，拥有五氟亚砜的烯二炔在癌症治疗中是很有前途的分子。
• NOVEL CYP-EICOSANOID DERIVATIVES
  申请人：MAX-DELBRÜCK-CENTRUM FÜR MOLEKULARE MEDIZIN

  公开号：US20170008918A1

  公开（公告）日：2017-01-12

  The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for C the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.

  本发明涉及一般式（I）的化合物，这些化合物是由细胞色素P450（CYP）酶从ω-3（n-3）多不饱和脂肪酸（PUFAs）产生的环氧代谢产物的类似物。本发明还涉及含有这些化合物中的一个或多个的组合物，以及利用这些化合物或组合物用于治疗或预防与炎症、增殖、高血压、凝血、免疫功能、病理性血管生成、心力衰竭和心律失常相关的疾病和症状。
• CYP-eicosanoid derivatives
  申请人：MAX-DELBRUECK-CENTRUM FUER MOLEKULARE MEDIZIN

  公开号：US11130772B2

  公开（公告）日：2021-09-28

  The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.

  本发明涉及根据通式（I）的化合物，它们是由细胞色素 P450（CYP）酶从欧米茄-3（n-3）多不饱和脂肪酸（PUFA）产生的环氧代谢物的类似物。本发明进一步涉及含有一种或多种这些化合物的组合物，以及这些化合物或组合物用于治疗或预防与炎症、增殖、高血压、凝血、免疫功能、病理性血管生成、心力衰竭和心律失常相关的病症和疾病。
• Novel acyclic enediynes inhibit Cyclin A and Cdc25C expression and induce apoptosis phenomenon to show potent antitumor proliferation
  作者：Yu-Hsiang Lo、I-Ling Lin、Chi-Fong Lin、Cheng-Chung Hsu、Sheng-Huei Yang、Shinne-Ren Lin、Ming-Jung Wu

  DOI：10.1016/j.bmc.2007.04.024

  日期：2007.7

  A series of acyclic enediynes showing significant inhibition on the growth of tumor cancer is disclosed. To investigate the structure-activity relationship, compounds 12-33 were synthesized. Among them, compound 17 showed most potent growth inhibition activity against all tumor cell lines at low concentration, such as SR (0.4 mu M) and MDA-MB-435 (0.8 mu M), and almost completely blocked cell cycle in G2/M phase via controlling Cyclin A and Cdc25C expression. On the other hand, compound 29 showed potent induced apoptosis activity by inducing activation of caspase-3, -8, and -9. Thus, this article disclosed a new multiple-protein regulator in cell cycle regulation and induced apoptosis to achieve the goal of anticancer drug. (c) 2007 Elsevier Ltd. All rights reserved.