1D-3-chloro-3-deoxy-myo-inositol | 143393-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1D-3-chloro-3-deoxy-myo-inositol
• 英文别名: D-3-Chloro-3-deoxy-myo-inositol；D-3-deoxy-3-chloro-myo-inositol
• CAS: 143393-84-4
• 化学式: C₆H₁₁ClO₅
• 分子量: 198.603
• InChiKey: BSMLUJHFZGTHOG-XCMZKKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1D-3-chloro-3-deoxy-myo-inositol 在 camphor-10-sulfonic acid sodium hydride 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 D-4,5,6-Tri-O-benzyl-3-chloro-3-deoxy-1,2-O-isopropylidene-myo-inositol
  参考文献：
  名称：

  Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol

  摘要：

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.

  DOI：

  10.1021/jo00084a010
• 作为产物：
  描述：

  1L-3,4:5,6-di-O-cyclohexylidene-2-O-methyl-1-O-trifluoromethylsulfonyl-chiro-inositol 在 咪唑 、 三溴化硼 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1D-3-chloro-3-deoxy-myo-inositol
  参考文献：
  名称：

  合成和评估3-修饰的1D-肌醇作为磷脂酰肌醇合酶的抑制剂和底物以及细胞摄取肌醇的抑制剂。

  摘要：

  合成了许多3-取代的1D-肌醇，并将其作为磷脂酰肌醇合酶和被完整细胞摄取的底物进行评估。1D-3-氨基-，-3-氯-和-3-（乙酰硫基）-3-脱氧-肌醇均通过亲核取代1L-1的6-O-（三氟甲基）磺酰基合成，通过与LiN3反应分别形成2：3,4-二-O-环己叉基-5-O-甲基-6-O-[（三氟甲基）-磺酰基]-手性肌醇，然后还原叠氮基官能团，并与LiCl和KSAc结合，得到O保护的化合物。使用BBr3进行O-脱甲基和伴随的乙缩醛水解提供了游离羟基的3-氨基-和3-氯-3-脱氧-1D-肌醇。3-巯基类似物是通过除去乙酰硫基类似物的缩醛基获得的，然后进行过乙酸的乙酰化和纯化，然后进行O-脱甲基和脱乙酰。通过Barton-McCombie脱氧从6-O-（咪唑-1-基硫代羰基）化合物合成3-脱氧衍生物。通过叠氮化物置换，由1L-1-O-甲苯磺酰基-手性肌醇直接合成3-叠氮基衍生物。3-酮类似物是通

  DOI：

  10.1021/jm00075a018

文献信息

• Probing the D-1,4,5-IP3/D-1,3,4,5-IP4 functional interface. Synthesis and pharmacology of novel D-3-modified myo-inositol trisphosphate analogues
  作者：Abdul H. Fauq、Alan P. Kozikowski、Vassil I. Ognyanov、Robert A. Wilcox、Stefan R. Nahorski

  DOI：10.1039/c39940001301

  日期：——

  To explore the biological significance of the D-3 position phosphorylation of the second messenger D-myo-inositol 1,4,5-trisphosphate (IP3) in cellular signalling, three novel D-3-substituted analogues of IP3 have been synthesized; their binding and Ca2+-release profiles at the IP3-receptor have been studied and shown to correlate with the steric requirement of the D-3 substituent.

  为了探索第二信使 D-肌醇-1,4,5-三磷酸酯（IP3）的 D-3 位磷酸化在细胞信号传导中的生物学意义，我们合成了三种新型 D-3 取代的 IP3 类似物；我们研究了它们在 IP3 受体上的结合和 Ca2+ 释放情况，结果表明它们与 D-3 取代基的立体要求相关。
• Synthesis and evaluation of 3-modified 1D-myo-inositols as inhibitors and substrates of phosphatidylinositol synthase and inhibitors of myo-inositol uptake by cells
  作者：Stephen C. Johnson、Jean Dahl、Tzenge Lien Shih、David J. A. Schedler、Laurens Anderson、Thomas L. Benjamin、David C. Baker

  DOI：10.1021/jm00075a018

  日期：1993.11

  evaluated as substrates for phosphatidylinositol synthase and uptake by intact cells. 1D-3-Amino-, -3-chloro-, and -3-(acetylthio)-3-deoxy-myo-inositols were all synthesized by nucleophilic displacement of the 6-O-(trifluoromethyl)sulfonyl group of 1L-1,2:3,4-di-O-cyclohexylidene-5-O-methyl-6-O-[(trifluoromethyl)-sulfon yl] - chiro-inositol (which was prepared from L-quebrachitol), respectively, by reaction

  合成了许多3-取代的1D-肌醇，并将其作为磷脂酰肌醇合酶和被完整细胞摄取的底物进行评估。1D-3-氨基-，-3-氯-和-3-（乙酰硫基）-3-脱氧-肌醇均通过亲核取代1L-1的6-O-（三氟甲基）磺酰基合成，通过与LiN3反应分别形成2：3,4-二-O-环己叉基-5-O-甲基-6-O-[（三氟甲基）-磺酰基]-手性肌醇，然后还原叠氮基官能团，并与LiCl和KSAc结合，得到O保护的化合物。使用BBr3进行O-脱甲基和伴随的乙缩醛水解提供了游离羟基的3-氨基-和3-氯-3-脱氧-1D-肌醇。3-巯基类似物是通过除去乙酰硫基类似物的缩醛基获得的，然后进行过乙酸的乙酰化和纯化，然后进行O-脱甲基和脱乙酰。通过Barton-McCombie脱氧从6-O-（咪唑-1-基硫代羰基）化合物合成3-脱氧衍生物。通过叠氮化物置换，由1L-1-O-甲苯磺酰基-手性肌醇直接合成3-叠氮基衍生物。3-酮类似物是通
• Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol
  作者：Alan P. Kozikowski、Garth Powis、Abdul H. Fauq、Werner Tuckmantel、Alfred Gallegos

  DOI：10.1021/jo00084a010

  日期：1994.3

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.