6-methylchromone-2-carbonyl chloride | 65843-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-methylchromone-2-carbonyl chloride
• 英文别名: 6-methyl-4-oxochromene-2-carbonyl chloride
• CAS: 65843-90-5
• 化学式: C₁₁H₇ClO₃
• 分子量: 222.628
• InChiKey: NSKVZNZAZJEHPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methylchromone-2-carbonyl chloride 在 溶剂黄146 、 N,N-二甲基苯胺 作用下， 以 乙腈 为溶剂， 生成 [[(4-Methylbenzoyl)amino]-[5-(6-methyl-4-oxochromen-2-yl)-1,3,4-oxadiazol-2-yl]methyl]phosphonic acid
  参考文献：
  名称：

  Synthesis of C-heteryl-substituted aminomethylphosphonic acids derivatives

  摘要：

  The available diethyl 5-hydrazino-2-p-tolyl-1,3-oxazol-1-ylphosphonate was readily acylated with chlorides of carboxylic acids of heterocyclic series. On heating in acetic acid it underwent the oxazole ring cleavage, recyclization and diethylation that was used to prepar the substituted 2-p-toluylaminomethylphosphonic acids containing a series of 2-heteryl-1,3,4-oxadiazol-5-yl residues in the alpha-position relative to the phosponyl group.

  DOI：

  10.1134/s1070363210040067
• 作为产物：
  描述：

  6-甲基色酮-2-羧酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-methylchromone-2-carbonyl chloride
  参考文献：
  名称：

  Co（iii）催化的烯烃与三异丙基甲硅烷基乙炔的Z选择性氧化C–H / C–H交叉偶联†

  摘要：

  提出了一种由Co（III）催化的丙烯酰胺与三异丙基甲硅烷基乙炔的直接氧化C–H / C–H交叉偶联反应。它适用于官能度宽泛的未取代的内部和末端丙烯酰胺。该方案的可行性已通过类固醇药物Epristeride衍生物的晚期炔基化成功证明。

  DOI：

  10.1039/c9cc02347j

文献信息

• Synthesis and evaluation of chromone-2-carboxamide derivatives as cytotoxic agents and 5-lipoxygenase inhibitors
  作者：Fatima Bousejra-ElGarah、Barbora Lajoie、Jean-Pierre Souchard、Geneviève Baziard、Jalloul Bouajila、Salomé El Hage

  DOI：10.1007/s00044-016-1691-y

  日期：2016.11

  potency to inhibit the proliferation of breast (MCF-7), ovarian (OVCAR and IGROV), and colon (HCT-116) cancer cell lines, was evaluated in vitro using the MTT assay. Among these compounds, 13 showed promising cytotoxic activity against at least one cancer cell line with IC50 in the range 0.9–10 μM. Our compounds were also screened for their anti-inflammatory activity as putative inhibitors of 5-lipoxygenase

  在本研究中，我们制备了一系列具有多种酰胺侧链的21色酮羧酰胺衍生物。使用MTT分析法在体外评估了它们抑制乳腺癌（MCF-7），卵巢癌（OVCAR和IGROV）和结肠癌（HCT-116）癌细胞系增殖的能力。在这些化合物中，有13种显示出对至少一种癌细胞的有希望的细胞毒活性，其IC 50为0.9-10μM。还筛选了我们的化合物作为5-脂氧合酶的抑制剂的抗炎活性。对色酮羧酰胺衍生物的结构-活性关系研究表明，色酮核（R 1）或丙基上存在6-氟取代基酰胺侧链上的3-乙基苯基（R 2）对细胞毒性活性有积极影响。就抗炎活性而言，亲水性色酮羧酰胺衍生物表现出更大的5-脂氧合酶抑制作用。色酮羧酰胺的理化性质符合药物开发过程的一般要求，配体效率值可进一步优化化合物结构。4b作为线索。
• [EN] NOVEL P-GLYCOPROTEIN INHIBITOR, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] INHIBITEUR DE P-GLYCOPROTEINE, PROCEDE DE PREPARATION, ET COMPOSITION PHARMACEUTIQUE LE RENFERMANT
  申请人：HANMI PHARM IND CO LTD

  公开号：WO2005033101A1

  公开（公告）日：2005-04-14

  A p-glycoprotein inhibitor of Formula 1 is capable of effectively preventing the development of multi-drug resistance directed to an anticancer agent in cancer cells, and greatly enhances the bioavailability of the drug, such as paclitaxel, which is not readily absorbed when orally administered.

  一种化学式为1的p-糖蛋白抑制剂能够有效地阻止癌细胞对抗癌药物产生的多药耐药性，并显著增强药物的生物利用度，例如紫杉醇，口服给药时不易被吸收。
• Payard; Tronche; Bastide, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 453 - 460
  作者：Payard、Tronche、Bastide、et al.

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands
  作者：Geneviève Baziard-Mouysset、Salouma Younes、Youssef Labssita、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard、Bruno Pfeiffer、Béatrice Guardiola-Lemaitre

  DOI：10.1016/s0223-5234(98)80001-9

  日期：1998.6

  Starling from a random screening showing that 2-[(4-benzylpiperazinyl)methyl] chromone was a selective and potent sigma ligand, a series of analogues were synthesized. Introduction of a substituent on the chromone moiety, replacement of methylenes by carbonyl groups and benzyl by aryl groups decrease the affinity for sigma sites. The result obtained after introduction of various substituents on the aromatic part of the benzyl is strictly depending on the size and on the position of these substituents. Stretching of the carbon chain between the phenyl and the piperazine does not strongly modify the affinity. 2-[4-(4'-methoxy benzyl)-1-piperazinyl methyl] chromone has been tested in behavioral tests that permit to believe that such derivatives could be interesting for the treatment of psychosis. (C) Elsevier, Paris.
• Costa, Ana M. B. S. R. C. S.; Dean, Francis M.; Jones, Michael A., Journal of the Chemical Society. Perkin transactions I, 1985, p. 799 - 808
  作者：Costa, Ana M. B. S. R. C. S.、Dean, Francis M.、Jones, Michael A.、Varma, Rajender S.

  DOI：——

  日期：——