2,3-dimethoxy-5-methyl-6-(13-hydroxytridecyl)-1,4-benzoquinone | 77712-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,3-dimethoxy-5-methyl-6-(13-hydroxytridecyl)-1,4-benzoquinone
• 英文别名: 6-(13-Hydroxytridecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone；2-(13-hydroxytridecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 77712-17-5
• 化学式: C₂₂H₃₆O₅
• 分子量: 380.525
• InChiKey: QKRIPFAYOUIPFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-dimethoxy-6-(12-methoxycarbonyldodecyl)-5-methyl-1,4-benzoquinone 在 三氯化铁 作用下， 以 甲醇 、 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 氯仿 、 水 为溶剂， 生成 2,3-dimethoxy-5-methyl-6-(13-hydroxytridecyl)-1,4-benzoquinone
  参考文献：
  名称：

  Method for therapy of ischemic disease

  摘要：

  患有缺血性疾病，如脑卒中、心脏功能不全、由于血管变化导致的肾功能不全等的哺乳动物，通过向该哺乳动物投予一定量的以下化合物来治疗：##STR1## 其中n为4至22的整数。

  公开号：

  US04436753A1

文献信息

• Synthesis of quinones having carboxy- and hydroxy-alkyl side chains, and their effects on rat-liver lysosomal membrane.
  作者：KAYOKO OKAMOTO、MASAZUMI WATANABE、MITSURU KAWADA、GIICHI GOTO、YASUKO ASHIDA、KATSUAKI ODA、AKIKO YAJIMA、ISUKE IMADA、HIROSHI MORIMOTO

  DOI：10.1248/cpb.30.2797

  日期：——

  In order to study the structure activity relationship of metabolites of ubiquinone, α-tocopherol and phylloquinone (Ia, b, c, IIa, b, c), 3-carboxy-2-butenyl (IIIa, b, c), 6-hydroxy-3-methyl-2-hexenyl (IVa, b, c), 4-hydroxy-3-methylbutyl (Va, b), 4-hydroxy-3-methyl-2-butenyl (VIb, c), ω-carboxyalkyl (VIIa, b, c), and ω-hydroxyalkyl (VIIIa, b) side chains were introduced into the 6-position of 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone and 2, 3, 5-trimethyl-1, 4-benzoquinone, as well as the 3-position of 2-methyl-1, 4-naphthoquinone. The effects of these quinones on the membrane stability of rat-liver lysosomes and on the activity of bovine heart phosphodiesterase were investigated. A good correlation was observed between these activities of the benzoquinone derivatives (VIIa, b).

  为了研究辅酶Q、α-生育酚和叶绿醌（Ia, b, c, IIa, b, c）的代谢产物结构活性关系，将3-羧基-2-丁烯基（IIIa, b, c）、6-羟基-3-甲基-2-己烯基（IVa, b, c）、4-羟基-3-甲基丁基（Va, b）、4-羟基-3-甲基-2-丁烯基（VIb, c）、ω-羧基烷基（VIIa, b, c）和ω-羟基烷基（VIIIa, b）侧链引入到2, 3-二甲氧基-5-甲基-1, 4-苯醌和2, 3, 5-三甲基-1, 4-苯醌的6-位以及2-甲基-1, 4-萘醌的3-位。研究了这些醌类化合物对大鼠肝脏溶酶体膜稳定性和牛心磷酸二酯酶活性的影响。苯醌衍生物（VIIa, b）的这些活性之间观察到了良好的相关性。
• Quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04559177A1

  公开（公告）日：1985-12-17

  A compound of the formula: ##STR1## wherein m is an integer of 11 to 22; R.sub.1 is alkyl having 1 to 4 carbon atoms; R.sub.2 is hydrogen, alkyl having 1 to 4 carbon atoms or carboxylic acyl having 1 to 8 carbon atoms. Such compounds have pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immuno-regulatory and lysosomal membrane stabilizing activity, and inhibit SRS-A production, and are useful as a heart failure remedy, cerebral circulation disturbance remedy, immuno-regulator, and antiallergic drug.

  一种化合物的化学式：##STR1## 其中m是11至22的整数；R.sub.1是具有1至4个碳原子的烷基；R.sub.2是氢，具有1至4个碳原子的烷基或具有1至8个碳原子的羧酸酰基。这些化合物具有药理活性，如降压、组织代谢刺激、免疫调节和溶酶体膜稳定活性，并抑制SRS-A的产生，可用作心力衰竭治疗、脑循环障碍治疗、免疫调节剂和抗过敏药物。
• 2,3-Dialkoxy-1,4-quinone derivatives; method of producing 1,4-quinone derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0021841A2

  公开（公告）日：1981-01-07

  A compound of the general formula: wherein m is an integer of 10 to 21; R1 is lower alkyl having 1 to 4 carbon atoms; B is a -CH2- or-CO- group, when B is-CH2-, R2 is hydrogen, lower alkyl having 1 to 4 carbon atoms or lower acyl having 1 to 8 carbon atoms, and when B is -CO-, R2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immunoregulatory, lysosomal membrane stablizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immunoregulatorand antiallergic drug. A compound of the general formula: [wherein each R3 is lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, or two R3's taken together represent -CH =CH-CH =CH-; n is O or an integer of 1 to 20 and when n is 1 to 20, A is -CH2-, or -CO- and Z is CH2OH, acyloxymethyl having 2 to 11 carbon atoms, esterified or unesterified carboxyl having 1 to 5 carbon atoms, lower alkoxymethyl having 2 to 5 carbon atoms, silyloxymethyl having 4 to 7 carbon atoms or acetalmethyl having 3 to 8 carbon atoms; when n is O, -A(CH2)n-Z is (wherein - is 0 or an integer of 1 to 12) and Z is H] can be produced with advantage for commercial-scale production by oxidising a compound of the general formula: [wherein X1 or X2 is hydroxyl or amino, with the other being H or an esterified hydroxyl group having 1 to 8 carbon atoms or etherified hydroxyl group having 2 to to 8 carbon atoms; the other symbols are as defined above] with oxygen or air in the presence of a transition metal complex compound.

  通式如下的化合物 其中 m 是 10 至 21 的整数；R1 是具有 1 至 4 个碳原子的低级烷基；当 B 为-CH2-时，R2 为氢、具有 1 至 4 个碳原子的低级烷基或具有 1 至 8 个碳原子的低级酰基；当 B 为-CO-时，R2 为氢或具有 1 至 4 个碳原子的低级烷基、具有降血压、促进组织代谢、免疫调节、稳定溶酶体膜和抑制 SRS-A 生成等药物活性，可用作治疗心力衰竭、脑循环障碍、免疫调节和抗过敏药物。通式如下的化合物 [其中每个 R3 是具有 1 至 4 个碳原子的低级烷基或具有 1 至 4 个碳原子的低级烷氧基，或两个 R3 共同代表-CH =CH-CH =CH-；n 是 O 或 1 至 20 的整数，当 n 为 1 至 20 时，A 是-CH2-、 或-CO-，Z 是 CH2OH、具有 2 至 11 个碳原子的酰氧基甲基、具有 1 至 5 个碳原子的酯化或未酯化羧基、具有 2 至 5 个碳原子的低级烷氧基甲基、具有 4 至 7 个碳原子的硅氧基甲基或具有 3 至 8 个碳原子的乙缩醛甲基；当 n 是 O 时，-A(CH2)n-Z 是 (其中 - 为 0 或 1 至 12 的整数），Z 为 H]，可通过氧化通式如下的化合物生产，具有商业规模生产的优势： [其中 X1 或 X2 为羟基或氨基，另一个为 H 或具有 1 至 8 个碳原子的酯化羟基或具有 2 至 8 个碳原子的醚化羟基；其他符号如上定义]，在过渡金属复合物存在下，与氧气或空气氧化。
• Benzoquinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0201196B1

  公开（公告）日：1991-07-03
• Medicinal compositions comprising as an active ingredient substituted 1,4-benzoquinones
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0031727B1

  公开（公告）日：1986-07-30