3β(tetrahydropyran-2'-yl)oxypregna-5,20(22)-diene | 38677-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β(tetrahydropyran-2'-yl)oxypregna-5,20(22)-diene
• 英文别名: 2-[[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-prop-1-en-2-yl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane
• CAS: 38677-14-4
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: TWLRHMYNNHCTBW-GPJQEICZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β(tetrahydropyran-2'-yl)oxypregna-5,20(22)-diene 在 palladium on activated charcoal 甲醇 、 硫酸 、 氢气 作用下， 生成 20-methyl-5α-pregnan-3β-ol
  参考文献：
  名称：

  20-Methylpregnane and Derivatives^1,2

  摘要：

  DOI：

  10.1021/jo01071a022
• 作为产物：
  描述：

  孕烯醇酮 在 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 叔丁醇 为溶剂， 生成 3β(tetrahydropyran-2'-yl)oxypregna-5,20(22)-diene
  参考文献：
  名称：

  Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia

  摘要：

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00193-2

文献信息

• Rabinowitz, Michael H.; Djerassi, Carl, Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 304 - 317
  作者：Rabinowitz, Michael H.、Djerassi, Carl

  DOI：——

  日期：——
• Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays
  作者：Rita Katoch、Shilpa S. Korde、K.D. Deodhar、Girish K. Trivedi

  DOI：10.1016/s0040-4020(98)01187-9

  日期：1999.2

  The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3 beta-ol-20S-yl)methyl]oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3- one-20S-yl)methyl]oate]-2',2',5'.5'-tetra methyl pyrrolidine-1'-oxyl, 3 "[(3 beta-acetoxypregn-5-en-20-one-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2 ",2 ",5 ",5 "-tetramethyl pyrrolidine-1 "-oxyl and 3 "-[(pregn-5-en-3,20-dione-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 20-Methylpregnane and Derivatives^1,2
  作者：JOHN P. DUSZA、WERNER BERGMANN

  DOI：10.1021/jo01071a022

  日期：1960.1
• Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia
  作者：Gang Zheng、Hui Li、Kathy Yang、Dana Blessington、Kai Licha、Sissel Lund-Katz、Britton Chance、Jerry D. Glickson

  DOI：10.1016/s0960-894x(02)00193-2

  日期：2002.6

  For monitoring low-density lipoprotein receptors (LDLr) in tumors and in livers of patients with familial hypercholesterolemia (FH) treated with gene therapy, a series of tricarbocyanine cholesteryl laurates were synthesized with the cholesteryl laurate moiety serving as the lipid-chelating anchor for low-density lipoprotein (LDL). One of these conjugates, TCL17, was successfully used to label LDL to give a new NIRF, TCL17-LDL. Ex vivo biological studies on an LDLr overexpressing tumor model, human hepatoblastoma G(2) (HepG(2)), confirmed that this NIRF were internalized selectively by the tumor and detected with high sensitivity by a low-temperature 3-D redox scanner. (C) 2002 Elsevier Science Ltd. All rights reserved.