2-methoxy-3-(2-oxoicosyloxy)propanol | 98383-92-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-methoxy-3-(2-oxoicosyloxy)propanol
• 英文别名: 3-(2-Oxoeicosyloxy)-2-methoxypropanol；1-(3-Hydroxy-2-methoxypropoxy)icosan-2-one
• CAS: 98383-92-7
• 化学式: C₂₄H₄₈O₄
• 分子量: 400.643
• InChiKey: GTNGUSHIEQSFKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  28
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-(2-oxoicosyloxy)propanol 以26%的产率得到
  参考文献：
  名称：

  UKAWA, KIYOSHI;IMAMIYA, EIKO;YAMAMOTO, HIROAKI;MIZUNO, KATSUTOSHI;TASAKA,+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1249-1255

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-环氧二十烷 生成 2-methoxy-3-(2-oxoicosyloxy)propanol
  参考文献：
  名称：

  NODZIMA, SESITI;NOMURA, XIROAKIRA;TSUSIMA, CYCYMY

  摘要：

  DOI：

文献信息

• Synthesis and antitumor activity of new alkylphospholipids containing modifications of the phosphocholine moiety.
  作者：Kiyoshi UKAWA、Eiko IMAMIYA、Hiroaki YAMAMOTO、Katsutoshi MIZUNO、Akihiro TASAKA、Zen-ichi TERASHITA、Tetsuya OKUTANI、Hiroaki NOMURA、Takashi KASUKABE、Motoo HOZUMI、Ichiro KUDO、Keizo INOUE

  DOI：10.1248/cpb.37.1249

  日期：——

  New antitumor alkylglycerophospholipids, in which primarily the phosphocholine moiety of the platelet activating factor (PAF) molecule was modified, were synthesized from 1-alkyl-2-substituted glycerols by introducing polar head phosphoryl groups having methylene bridges of various lengths (from 2 to 14 carbons). They were tested for PAF agonistic activity and antitumor properties. In a series of 1-octadecyl-2-acetoacetylglycerophospholipids (1a-f), an increase in the length of the methylene bridge separating the phosphate and trimethylammonio group in the polar head side chain at position 3 of the glycerol backbone resulted in a progressive decrease in PAF agonistic activity and a characteristic change in antitumor activity against human promyelocytic leukemia cells (HL-60). Maximal potency was obtained with the compound having a decamethylene bridge (1e, IC50 value=1.5 μg/ml). Thus, alkylphospholipids possessing a decanmethylene bridge and a variety of substituents at position 2 (1g-n) were synthesized. They showed potent inhibitory activity with IC50 values ranging from 0.4 to 1.9 μg/ml, depending on the nature of the 2-substituent in the phospholipid molecule. In in vivo tests of the present series of alkylglycerophospholipids (1a-n), using mice bearing sarcoma 180 and mice with mammary carcinoma MM46 (both cells and compounds were given i.p.), 1-octadecyl-2-acetoacetyl-3-glyceryl ω-trimethylammoniodecyl phosphate (1e) showed the most potent life-prolonging effect. The structure-activity relationships are discussed.

  新型抗肿瘤烷基甘油磷脂是通过对血小板活化因子（PAF）分子中的磷酸胆碱部分进行修饰，从1-烷基-2-取代甘油中合成而得。通过引入具有不同长度（从2到14个碳）的亚甲基桥的极性头部磷酰基团进行了合成，并测试了其对PAF激动活性和抗肿瘤性质的影响。在一系列1-十八烷基-2-乙酰乙酰甘油磷脂（1a-f）中，随着甘油主链位置3处的磷酸和三甲铵基团之间的亚甲基桥长度增加，PAF激动活性逐渐降低，对人类早幼粒白血病细胞（HL-60）的抗肿瘤活性也发生了特征性变化。通过具有癸二烯桥的化合物（1e，IC50值=1.5μg/ml）获得了最大效力。因此，合成了具有癸二烯桥和在位置2具有各种取代基的烷基磷脂（1g-n）。它们表现出强烈的抑制活性，IC50值范围从0.4到1.9μg/ml，具体取决于磷脂分子中2-取代基的性质。在体内测试中，通过使用携带肉瘤180的小鼠和携带乳腺瘤MM46的小鼠（两种细胞和化合物均以腹腔途径给予），1-十八烷基-2-乙酰乙酰-3-甘油ω-三甲铵癸二烯磷酸酯（1e）表现出最强的延长寿命效果。讨论了结构-活性关系。
• Ketoalkylphospholipids
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04649203A1

  公开（公告）日：1987-03-10

  Novel ketoalkylphospholipids, inclusive of salts thereof, of the formula ##STR1## wherein R.sup.1 is an aliphatic hydrocarbon residue containing 10 to 20 carbon atoms, R.sup.2 is hydrogen or methoxy, and R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-5 alkyl, or ##STR2## represents a cyclic ammonio group, exhibit inhibitory activity against multiplication of tumor cells and antifungal activity.

  新型酮烷基磷脂类化合物，包括其盐，化学式如下：其中R.sup.1为含有10至20个碳原子的脂肪烃残基，R.sup.2为氢或甲氧基，R.sup.3、R.sup.4和R.sup.5独立地为氢或C.sub.1-5烷基，或##STR2##代表环铵基团，表现出抑制肿瘤细胞增殖和抗真菌活性。
• Ketoalkylphospholipids and their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0138559A2

  公开（公告）日：1985-04-24

  @ Novel ketoalkylphospholipids, inclusive of salts thereof, of the formula wherein R1 is an aliphatic hydrocarbon residue containing 10 to 20 carbon atoms, R2 is hydrogen or methoxy, and R3, R4 and R5 are independently hydrogen or C1-5 alkyl, or represents a cylic ammonio group, exhibit inhibitory activity against multiplication of tumor cells and antifungal activity.

  @ 新型酮烷基磷脂，包括其盐，其式为 式中 R1 是含有 10 至 20 个碳原子的脂族烃残基、 R2 是氢或甲氧基，以及 R3、R4 和 R5 独立地为氢或 C1-5 烷基，或 代表环氨基团，具有抑制肿瘤细胞繁殖的活性和抗真菌活性。
• Phospholipid derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0225129A1

  公开（公告）日：1987-06-10

  Phospholipid derivatives of the formula: wherein R¹ is a higher alkyl, acylmethyl or alkylcarbamoyl group which may be substituted by cycloalkyl; R² is a lower alkyl which may be substituted by carboxy, formyl or lower acyl, a carbamcyl or thiocarbamoyl group which is substituted by lower alkyl, or an acetoacetyl group; R³, R⁴ and R⁵ are independently hydrogen or lower alkyl, or represents a cyclic ammonio group; and n represents an integer of 8 to 14, and salts thereof have antitumor activity and platelet activating factor inhibitory activity and are useful as antitumor agents.

  式中的磷脂衍生物： 其中 R¹ 是可被环烷基取代的高烷基、酰甲基或烷基氨基甲酰基；R² 是可被羧基、甲酰基或低级酰基、被低级烷基取代的氨基甲酰基或硫代氨基甲酰基或乙酰乙酰基取代的低级烷基；R³、R⁴ 和 R⁵ 独立地为氢或低级烷基，或代表环氨基团；n 代表 8 至 14 的整数。 代表环状铵基；以及 n 代表 8 至 14 的整数，其盐类具有抗肿瘤活性和血小板活化因子抑制活性，可用作抗肿瘤剂。
• UKAWA, KIYOSHI;IMAMIYA, EIKO;YAMAMOTO, HIROAKI;MIZUNO, KATSUTOSHI;TASAKA,+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1249-1255
  作者：UKAWA, KIYOSHI、IMAMIYA, EIKO、YAMAMOTO, HIROAKI、MIZUNO, KATSUTOSHI、TASAKA,+

  DOI：——

  日期：——