3-(heptyloxy)benzoic acid | 108807-04-1

• 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: 3-(heptyloxy)benzoic acid
• 英文别名: 3-Heptyloxy-benzoesaeure；m-heptyloxybenzoic acid；3-heptoxybenzoic acid
• CAS: 108807-04-1
• 化学式: C₁₄H₂₀O₃
• mdl: MFCD00871555
• 分子量: 236.311
• InChiKey: FOFZVIUYGPBWLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(heptyloxy)benzoic acid 在 氯化亚砜 、 三氟化硼乙醚 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 124.83h， 生成 methyl 3-[4-(3-heptyloxybenzoyl)-1,3,5-trimethylpyrrol-2-yl]propionate
  参考文献：
  名称：

  吡咯烷酸衍生物作为微粒体前列腺素E 2合酶-1的有害抑制剂

  摘要：

  微粒体前列腺素E 2合酶1（mPGES-1）是一种在炎症反应期间被诱导的酶。因此，该酶的抑制剂被认为是潜在的抗炎药。我们确定了3-（4-十二烷酰基-1,3,5-三甲基吡咯-2-基）丙酸（12）作为mPGES-1的亚微摩尔抑制剂。出乎意料的是，围绕该前导物的结构变化仅导致酶抑制效能的相对较小的变化。据报道，这种平坦的结构-活性关系通常是所谓的令人讨厌的抑制剂，它们不是通过直接与酶结合而发挥作用，而是通过在微摩尔浓度（有时甚至是亚微摩尔浓度）形成胶体状聚集体，从而以某种方式隔离并抑制了酶的靶标。没有专一性。由于基于聚集体的抑制作用对非离子型清洁剂（例如Triton X-100）高度敏感，因此，我们也研究了一些在这种清洁剂存在下能抑制人重组mPGES-1的化合物。吡咯衍生物12，67和81当添加0.1％的去污剂时，在Triton X-100不存在的情况下，IC 50值在0.1和1μM范围内时，其

  DOI：

  10.1016/j.ejmech.2011.12.009
• 作为产物：
  描述：

  methyl 3-(heptyloxy)benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(heptyloxy)benzoic acid
  参考文献：
  名称：

  Amphipathic benzoic acid derivatives: Synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC

  摘要：

  The first committed step in lipid A biosynthesis is catalyzed by uridine diphosphate-(3-O-(R-3-hydroxymyristoyl))--Nacetylglucosamine deacetylase (LpxC), a zinc-dependent deacetylase, and inhibitors of LpxC may be useful in the development of antibacterial agents targeting a broad spectrum of Gram-negative bacteria. Here, we report the design of amphipathic benzoic acid derivatives that bind in the hydrophobic tunnel in the active site of LpxC. The hydrophobic tunnel accounts for the specificity of LpxC toward substrates and substrate andlogues bearing a 3-O-myristoyl substituent. Simple benzoic acid derivatives bearing an aliphatic 'tail' bind in the hydrophobic tunnel with micromolar affinity despite the lack of a glucosamine ring like that of the substrate. However, although these benzoic acid derivatives each contain a negatively charged carboxylate 'warhead' intended to coordinate to the active site zinc ion, the 2.25 angstrom resolution X-ray crystal structure of LpxC complexed with 3-(heptyloxy)benzoate reveals 'backward' binding in the hydrophobic tunnel, such that the benzoate moiety does not coordinate to zinc. Instead, it binds at the outer end of the hydrophobic tunnel. Interestingly, these ligands bind with affinities comparable to those measured for more complicated substrate analogue inhibitors containing glucosamine ring analogues and hydroxamate 'warheads' that coordinate to the active site zinc ion. We conclude that the intermolecular interactions in the hydrophobic tunnel dominate enzyme affinity in this series of benzoic acid derivatives. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.01.044

文献信息

• Hypoglycemic agent
  申请人：Ajinomoto Co., Inc.

  公开号：US20030191323A1

  公开（公告）日：2003-10-09

  The present invention provides a hypoglycemic agent containing an acylsulfonamide derivative such as a compound of the following formula or an analog thereof, which agent is usable for preventing and curing diabetes: 1

  本发明提供一种含有酰磺酰胺衍生物的降糖剂，例如以下式的化合物或其类似物，该剂可用于预防和治疗糖尿病：
• Condensed pyrrolo derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0425134A1

  公开（公告）日：1991-05-02

  A heterocyclic compound of the formula (I): and a pharmacologically acceptable salt thereof which have platelet activating factor (PAF) antagonizing activity are disclosed.

  公开了一种具有血小板活化因子（PAF）拮抗活性的化学式（I）的杂环化合物及其药理学上可接受的盐。
• Acylsulfonamide derivative
  申请人：Ajinomoto Co., Inc.

  公开号：US06555584B1

  公开（公告）日：2003-04-29

  This invention provides a novel acylsulfonamide derivative which can be used as an ACC activity inhibitor effective for the treatment of visceral fat syndrome that becomes the risk-factor of diseases of adult people such as myocardial infarction, cerebral infarction and diabetes. Particularly, it relates to an acylsulfonamide derivative represented by a general formula 1 wherein R1 is substituted/unsubstituted C2-C12 alkyl or alkoxy group or substituted/unsubstituted C2-C12 alkenyl or alkynyl group, R2 is hydrogen atom, hydroxyl group, mercapto group, substituted/unsubstituted C1-C6 alkoxy or alkylthio group, nitro group, halogen atom, trichloromethyl group, trifluoromethyl group or cyano group, R3 is substituted/unsubstituted C1-C20 alkyl or alkoxy group, substituted/unsubstituted C2-C20 alkenyl or alkynyl group, substituted/unsubstituted aromatic hydrocarbon or aromatic heterocyclic group, substituted amino group, substituted/unsubstituted C2-C20 alkenyloxy or alkynyloxy group or R4O— (wherein R4 is substituted/unsubstituted aromatic hydrocarbon or aromatic heterocyclic group), Y is —CH═CH—, —N═CH—, —CH═N—, sulfur or oxygen, and ring A is aromatic hydrocarbon, aromatic heterocyclic ring or cyclic alkyl group.

  这项发明提供了一种新型的酰磺酰胺衍生物，可用作 ACC 活性抑制剂，有效用于治疗内脏脂肪综合征，该综合征成为成年人疾病的风险因素，如心肌梗塞、脑梗塞和糖尿病。特别地，它涉及一种由通式 1 表示的酰磺酰胺衍生物，其中 R1 是取代/未取代的 C2-C12 烷基或烷氧基或取代/未取代的 C2-C12 烯基或炔基，R2 是氢原子、羟基、巯基、取代/未取代的 C1-C6 烷氧基或烷硫基、硝基、卤原子、三氯甲基基团、三氟甲基基团或氰基，R3 是取代/未取代的 C1-C20 烷基或烷氧基、取代/未取代的 C2-C20 烯基或炔基、取代/未取代的芳香烃或芳香杂环基、取代氨基、取代/未取代的 C2-C20 烯氧基或炔氧基或 R4O—（其中 R4 是取代/未取代的芳香烃或芳香杂环基），Y 是—CH═CH—、—N═CH—、—CH═N—、硫或氧，环 A 是芳香烃、芳香杂环环或环状烷基。
• Optical compensatory sheet and liquid crystal display
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US05518783A1

  公开（公告）日：1996-05-21

  Disclosed is an optical compensatory sheet comprising a transparent support and an optically anisotropic layer provided thereon and having an optic axis inclined at 20 to 34 degrees from the normal of the sheet, wherein the optically anisotropic layer is formed from a discotic compound capable of forming a discotic nematic phase and an organic compound which has compatibility with the discotic compound and is capable of lowering a transition temperature of the discotic nematic phase by at least 10.degree. C. Further, a liquid crystal display provided with the optical compensatory sheet is disclosed.

  公开了一种光学补偿片，包括透明支撑体和在其上提供的具有光轴相对于片的法线倾斜20至34度的光学各向异性层，其中所述光学各向异性层由能够形成圆盘状向列相的圆盘状化合物和与该圆盘状化合物相容且能够将圆盘状向列相的转变温度降低至少10°C的有机化合物形成。此外，还公开了配有该光学补偿片的液晶显示器。
• Compounds and Compositions for the Treatment of Cancer
  申请人：Gagnon Lyne

  公开号：US20130217645A1

  公开（公告）日：2013-08-22

  New uses for phenylketone carboxylate compounds and substituted aromatic compounds of Formula I, Formula I.1, Formula I.2, Formula IA, Formula IB, Formula IC and Formula II and their pharmaceutical acceptable salts for the treatment of cancer. The use of a combination of two of these compounds is described and the use of the combination of one of these compounds with an anticancer agent such as decarbazine, doxorubicin, daunorubicin, cyclophosphamide, busulfex, busulfan, vinblastine, vincristine, bleomycin, etoposide, topotecan, irinotecan, taxotere, taxol, 5-fluorouracil, methotrexate, gemcitabine, cisplatin, carboplatin and chlorambucil.

  苯丙酮羧酸酯化合物和式I、式I.1、式I.2、式IA、式IB、式IC和式II以及它们的药用盐的新用途是治疗癌症。描述了使用其中两种化合物的组合，以及将其中一种化合物与抗癌药物（如去甲嘧啶、多柔比星、多柔比霉素、环磷酰胺、丁磺酰氮芥、丁磺酰胺、长春新碱、长春瑞滨、卡铂、依托泊苷、托泊替康、伊立替康、紫杉醇、紫杉烷、5-氟尿嘧啶、甲氨蝶呤、吉西他滨、顺铂和氯氨苷）组合使用的用途。