1-(2'-bromophenyl)-hexan-1-one | 864516-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2'-bromophenyl)-hexan-1-one
• 英文别名: 1-(2-bromophenyl)hexane-1-one；1-(2-Bromophenyl)hexan-1-one
• CAS: 864516-83-6
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: PIBOOSJZGZLPDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2'-bromophenyl)-hexan-1-one 在 三正丁胺 、 palladium diacetate 、 对甲苯磺酸 、 三(邻甲基苯基)磷 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 (5S,6R,E)-methyl 8-(2-hexanoylphenyl)-5,6-dihydroxyoct-7-enoate
  参考文献：
  名称：

  Synthesis of Bifunctional Lipoxin‐Derived Enzyme‐Triggered CO‐Releasing Molecules (LipET‐CORMs)

  摘要：

  AbstractIn an attempt to develop new anti‐inflammatory agents which act by co‐release of carbon monoxide (CO) and a specialized pro‐resolving mediator, we designed conjugates of a lipoxin A4 analogue and an acyloxycyclohexadiene‐Fe(CO)3 complex as an esterase‐triggered CO‐releasing molecule (ET‐CORM). After adjustment of the protecting group strategy, two of such compounds were successfully prepared by total synthesis (12 steps; 4–5 % overall yield) starting from deoxy‐d‐ribose and exploiting a Wittig olefination and an intermolecular Heck reaction as key C−C bond‐forming steps. A crucial late reduction of an aryl‐ketone moiety in the presence of a highly sensitive dienol ester functionality was achieved with BH3‐SMe2 in the presence of catalytic amounts of NaBH4. Both target compounds were dose‐dependently toxic towards cultured human umbilical vein endothelial cells (HUVEC), with LipET‐CORM 1‐A being slightly more toxic. While induction of heme oxygenase 1 (HO‐1) in HUVEC was observed for both compounds, they did not inhibit TNF‐α‐mediated VCAM‐1 expression in these cells. In M2 polarized macrophages HO‐1 expression was more pronounced as compared to M1 polarized macrophages. In both types of macrophages HO‐1 expression was downregulated by lipopolysaccharide, but only in M2 macrophages HO‐1 expression was rescued by LipET‐CORM. 15‐Lipoxygenase (15‐LO) was only expressed in M2 macrophages and was not influenced by LipET‐CORM. Collectively our data demonstrate that LipET‐CORMs induce HO‐1 expression in endothelial cells and M2 polarized macrophages. The role of the intra‐cellular released lipoxin A4 in resolution of inflammation, however, remains to be assessed.

  DOI：

  10.1002/ejoc.202201424
• 作为产物：
  描述：

  1-溴戊烷 在 戴斯-马丁氧化剂 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(2'-bromophenyl)-hexan-1-one
  参考文献：
  名称：

  Synthesis of Bifunctional Lipoxin‐Derived Enzyme‐Triggered CO‐Releasing Molecules (LipET‐CORMs)

  摘要：

  AbstractIn an attempt to develop new anti‐inflammatory agents which act by co‐release of carbon monoxide (CO) and a specialized pro‐resolving mediator, we designed conjugates of a lipoxin A4 analogue and an acyloxycyclohexadiene‐Fe(CO)3 complex as an esterase‐triggered CO‐releasing molecule (ET‐CORM). After adjustment of the protecting group strategy, two of such compounds were successfully prepared by total synthesis (12 steps; 4–5 % overall yield) starting from deoxy‐d‐ribose and exploiting a Wittig olefination and an intermolecular Heck reaction as key C−C bond‐forming steps. A crucial late reduction of an aryl‐ketone moiety in the presence of a highly sensitive dienol ester functionality was achieved with BH3‐SMe2 in the presence of catalytic amounts of NaBH4. Both target compounds were dose‐dependently toxic towards cultured human umbilical vein endothelial cells (HUVEC), with LipET‐CORM 1‐A being slightly more toxic. While induction of heme oxygenase 1 (HO‐1) in HUVEC was observed for both compounds, they did not inhibit TNF‐α‐mediated VCAM‐1 expression in these cells. In M2 polarized macrophages HO‐1 expression was more pronounced as compared to M1 polarized macrophages. In both types of macrophages HO‐1 expression was downregulated by lipopolysaccharide, but only in M2 macrophages HO‐1 expression was rescued by LipET‐CORM. 15‐Lipoxygenase (15‐LO) was only expressed in M2 macrophages and was not influenced by LipET‐CORM. Collectively our data demonstrate that LipET‐CORMs induce HO‐1 expression in endothelial cells and M2 polarized macrophages. The role of the intra‐cellular released lipoxin A4 in resolution of inflammation, however, remains to be assessed.

  DOI：

  10.1002/ejoc.202201424

文献信息

• Unexpected Role of <i>p</i>-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
  作者：Jiajia Chen、Wei Guo、Zhenrong Wang、Lin Hu、Fan Chen、Yuanzhi Xia

  DOI：10.1021/acs.joc.6b00844

  日期：2016.7.1

  The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration

  的反应p -toluenesulfonylmethyl胩（TOSMIC）用α-溴代化合物有效地导致α-磺化酮，酯和酰胺的报道，其中TOSMIC作为磺酰化剂的显式的新角色被揭露首次。通过对照实验和DFT计算进行的机理研究表明，该反应是由Cu（OTf）2催化的TOSMIC水合引发的，形成了甲酰胺中间体，该中间体在Cs 2 CO 3添加剂的介导下易于进行C-S键裂解。
• The intramolecular reaction of acetophenone <i>N</i>-tosylhydrazone and vinyl: Brønsted acid-promoted cationic cyclization toward polysubstituted indenes
  作者：Zhixin Wang、Yang Li、Fan Chen、Peng-Cheng Qian、Jiang Cheng

  DOI：10.1039/d0cc07966a

  日期：——

  TsNHNH2, a Brønsted acid-promoted intramolecular cyclization of o-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydic N-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, where N-tosylhydrazone served

  在存在TsNHNH 2的情况下，开发了布朗斯台德酸促进的邻-（1-芳基乙烯基）苯乙酮衍生物的分子内环化反应，导致多取代的茚并酮具有复杂性和多样性，产率中等至优异。与自由基或卡宾涉及醛基N-甲苯磺酰hydr与乙烯基的环化形成鲜明对比，涉及阳离子环化途径，其中N-甲苯磺酰zone在该转化过程中用作亲电试剂和烷基化试剂。
• [EN] NEW ARYL IMIDAZOLES AND RELATED COMPOUNDS AS C5A RECEPTOR MODULATORS<br/>[FR] ARYL IMIDAZOLES ET COMPOSES ASSOCIES, MODULATEURS DE RECEPTEUR C5A
  申请人：NEUROGEN CORP

  公开号：WO2003082829A1

  公开（公告）日：2003-10-09

  The invention provides Aryl substituted imidazoles, pyrazoles, pyridizines and related compounds of the Formula (I) where the ring system represented by Formula (A) is a 5 membered heteroaryl ring system, in which x is 0, A is chosen from carbon and heteroatoms nitrogen, oxygen, and sulfur, and E and G are independently carbon or nitrogen, provided that the 5 membered heteroaryl ring system does not contain more than 3 heteroatoms or more than 1 oxygen or sulfur atom, or a 6 membered heteroaryl ring system, in which x is 1, A, B, E, and G are independently chosen from carbon and nitrogen, provided that the 6 membered heteroaryl ring system does not contain more than 3 nitrogen atoms. The remaining variables, Ar1, Ar2, R, R1, R2, R3, R4, R5, R6, y and z are defined herein. Such compounds are ligands of C5a receptors. Preferred compounds of the invention act bind to C5a receptors with high affinity and exhibit neutral antagonist or inverse agonist activity at C5a receptors. This invention also relates to pharmaceutical compositions comprising such compounds. It further relates to the use of such compounds in treating a variety of inflammatory and immune system disorders.

  该发明提供了式（I）中的芳基取代咪唑、吡唑、吡啶和相关化合物，其中由式（A）表示的环系统是一个5成员杂芳基环系统，在该环系统中x为0，A从碳和杂原子氮、氧和硫中选择，E和G分别为碳或氮，前提是5成员杂芳基环系统不含超过3个杂原子或超过1个氧或硫原子，或者是一个6成员杂芳基环系统，在该环系统中x为1，A、B、E和G分别从碳和氮中选择，前提是6成员杂芳基环系统不含超过3个氮原子。其余变量Ar1、Ar2、R、R1、R2、R3、R4、R5、R6、y和z在此处定义。这些化合物是C5a受体的配体。该发明的优选化合物具有高亲和力结合到C5a受体，并且在C5a受体上表现为中性拮抗剂或逆激动剂活性。该发明还涉及包含这些化合物的药物组合物。它进一步涉及使用这些化合物治疗各种炎症和免疫系统疾病。
• Benzo lipoxin analogues
  申请人：Petasis A. Nicos

  公开号：US20050203184A1

  公开（公告）日：2005-09-15

  Benzolipoxin analogs, methods of their preparation and pharmaceutical compositions containing the compounds are provided. The compounds and compositions are useful in methods for treatment of various diseases, including, inflammation, autoimmune disease and abnormal cell proliferation.

  提供苯唑啉类似物、其制备方法以及含有这些化合物的药物组合物。这些化合物和组合物在治疗各种疾病的方法中非常有用，包括炎症、自身免疫疾病和异常细胞增殖。
• Aromatic Lipoxin A₄ and Lipoxin B₄ Analogues Display Potent Biological Activities
  作者：Timothy P. O'Sullivan、Karl S. A. Vallin、Syed Tasadaque Ali Shah、Jérôme Fakhry、Paola Maderna、Michael Scannell、Andre L. F. Sampaio、Mauro Perretti、Catherine Godson、Patrick J. Guiry

  DOI：10.1021/jm060270d

  日期：2007.11.1

  aromatic LXA4 and LXB4 analogues by employing Sharpless epoxidation, Pd-mediated Heck coupling, and diastereoselective reduction as the key transformations. Subsequent biological testing has shown that these analogues display potent biological activities. Phagocytic clearance of apoptotic leukocytes plays a critical role in the resolution of inflammation. Both LXA4 analogues (1R)-3a and (1S)-3a were

  脂蛋白是一组通常通过跨细胞脂氧合酶活性形成的生物活性类花生酸。在多种炎症条件下均已检测到脂氧合蛋白A4（LXA4）和脂氧合蛋白B4（LXB4）的生物合成。天然脂毒素LXA4和LXB4表现出有效的抗炎和分解生物作用。然而，它们的治疗潜力受到PG脱氢酶介导的氧化和还原作用的快速代谢失活的影响。在这里，我们报告通过采用Sharpless环氧化，Pd介导的Heck偶联和非对映选择性还原作为关键转化，对芳香族LXA4和LXB4类似物进行立体选择性合成。随后的生物学测试表明，这些类似物显示出强大的生物学活性。凋亡性白细胞的吞噬清除在炎症消退中起关键作用。发现LXA4类似物（1R）-3a和（1S）-3a均能刺激巨噬细胞吞噬凋亡性多形核白细胞（PMN）的吞噬作用显着增加，其功效与天然LXA4相当，尽管效力更高，而LXB4类似物还刺激吞噬作用，在10-11 M时观察到最大作用。LX刺激的吞噬作用与肌动蛋白细