S-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl) ethanethioate | 340701-35-1

• 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: S-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl) ethanethioate
• 英文别名: S-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)ethanethioate；trans,trans-farnesyl thioacetate；S-farnesylthioacetic acid；farnesylthiolacetate；POP-3MB-FC；Thioacetic acid S-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienyl) ester；S-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] ethanethioate
• CAS: 340701-35-1
• 化学式: C₁₇H₂₈OS
• 分子量: 280.475
• InChiKey: HCAXFXKDAVLSIG-NCZFFCEISA-N

物化性质

• 溶解度：
  易溶于可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl) ethanethioate 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.17h， 生成 S-(farnesyl-3-thio)propionitrile
  参考文献：
  名称：

  Structure-activity studies on the retinal rod outer segment isoprenylated protein methyltransferase

  摘要：

  Structure-activity studies were performed on the retinal rod outer segment isoprenylated protein methyltransferase that transfers a methyl group from S-adenosylmethionine (AdoMet) to the carboxyl group of isoprenylated (farnesylated or geranylgeranylated) cysteine residues. This methyltransferase enzyme has been shown to methylate N-acetyl-S-farnesyl-L-cysteine (L-AFC, 1) and S-(farnesyl-3-thio)propionic acid (FTP, 2). It is shown here that the enzyme does not enzymatically process D-AFC (8), although D-AFC (8) is a mixed-type inhibitor of the enzyme. Small modifications in the FTP (2) structural series generally lead to inactive substrates. For example, neither the cis- nor the trans-acrylate derivatives of FTP (2) are substrates of the enzyme, but both are inhibitors of it. Alkyl substitutions at the 3-position of FTP (2), moreover, lead to inhibitors of the methyltransferase. Substituents at the 2-position of FTP (2), as in 2-methyl-S-(farnesyl-3-thio)propionic acid (MFTP, 28) or S-farnesyl-2-(thiomethyl)acrylic acid (FTMA, 31), produce active substrates. Modifications at the carboxyl moiety produce neither substrates nor inhibitors of the enzyme. The conclusion from this and earlier studies is that the methyltransferase is selective for an isoprenylated thiopropionate moiety. Small deviations from this minimally essential structure lead to the abolition of substrate activity.

  DOI：

  10.1021/ja00036a052
• 作为产物：
  描述：

  反式,反式-金合欢醇 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到S-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl) ethanethioate
  参考文献：
  名称：

  Antiparasitic Activity of Sulfur- and Fluorine-Containing Bisphosphonates against Trypanosomatids and Apicomplexan Parasites

  摘要：

  基于2-烷基（氨基）乙基-1,1-双膦酸酯与克鲁兹锥虫法尼基二磷酸合成酶的晶体学数据，设计、合成了一些线性1,1-双膦酸及其他密切相关的衍生物，并对其在针对克鲁兹锥虫（造成查加斯病的病原体）和弓形虫（造成弓形虫病的病原体）的生物活性进行了评估，同时也针对克鲁兹锥虫（TcFPPS）和弓形虫（TgFPPS）的目标酶法尼基焦磷酸合成酶进行评估。含异戊烯基的1,1-双膦酸酯表现出适度的抗寄生虫活性，而线性α-氟-2-烷基（氨基）乙基-1,1-双膦酸酯则出人意料地缺乏抗寄生虫活性。尽管未表现出有效的抗寄生虫活性，这些数据对于建立结构活性关系却显得非常重要。

  DOI：

  10.3390/molecules22010082

文献信息

• Antisense modulation of isoprenylcysteine carboxyl methyltransferase expression
  申请人：Isis Pharmaceuticals Inc.

  公开号：US20030228688A1

  公开（公告）日：2003-12-11

  Antisense compounds, compositions and methods are provided for modulating the expression of isoprenylcysteine carboxyl methyltransferase. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding isoprenylcysteine carboxyl methyltransferase. Methods of using these compounds for modulation of isoprenylcysteine carboxyl methyltransferase expression and for treatment of diseases associated with expression of isoprenylcysteine carboxyl methyltransferase are provided.

  提供了用于调节异戊二烯基半胱氨酸羧甲基转移酶表达的反义物化合物、组合物和方法。这些组合物包括针对编码异戊二烯基半胱氨酸羧甲基转移酶的核酸的反义物化合物，特别是反义寡核苷酸。提供了利用这些化合物调节异戊二烯基半胱氨酸羧甲基转移酶表达并治疗与异戊二烯基半胱氨酸羧甲基转移酶表达相关的疾病的方法。
• [EN] S-FTA AND S-FTA ANALOGUES CAPABLE OF INHIBITING RETINOL-DEPENDENT RBP4-TTR INTERACTION FOR TREATMENT OF AGE-RELATED MACULAR DEGENERATION, STARGARDT DISEASE, AND OTHER RETINAL DISEASE CHARACTERIZED BY EXCESSIVE LIPOFUSCIN ACCUMULATION<br/>[FR] S-FTA ET ANALOGUES DE S-FTA POUVANT INHIBER L'INTERACTION DE RBP4-TTR DÉPENDANTE DU RÉTINOL POUR LE TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE LIÉE À L'ÂGE, DE LA MALADIE DE STARGARDT ET D'AUTRES MALADIES DE LA RÉTINE CARACTÉRISÉES PAR UNE ACCUMULATION EXCESSIVE DE LIPOFUSCINE
  申请人：UNIV COLUMBIA

  公开号：WO2013166040A1

  公开（公告）日：2013-11-07

  A method for treating a disease characterized, by excessive lipofuscin accumulation in the retina in a mammal afflicted therewith comprising administering to the mammal an effective amount of a compound having the structure (I), wherein X is O or S, or an ester or a pharmaceutically acceptable salt thereof.

  一种治疗哺乳动物视网膜中过度脂褐质积累所表现的疾病的方法，包括向哺乳动物施用化合物(I)的有效量，其中X为O或S，或其酯或药用可接受的盐。
• CATIONIC DRY POWDERS COMPRISING MAGNESIUM SALT
  申请人：Pulmatrix Operating Company, Inc.

  公开号：EP3470057A1

  公开（公告）日：2019-04-17

  The invention relates to respirable dry particles that contain one or more divalent metal cations, such as calcium, in an amount of less than 3% by weight, and to dry powders that contain the respirable particles. The dry particles can further contain an active agent, or can be used as carrier particles to deliver an active agent.

  本发明涉及含有一种或多种二价金属阳离子（如钙）且含量小于 3% （按重量计）的可吸入干颗粒，以及含有这种可吸入颗粒的干粉。干粉颗粒可进一步含有活性剂，或用作输送活性剂的载体颗粒。
• Monovalent metal cation dry powders for inhalation
  申请人：Pulmatrix Operating Company, Inc.

  公开号：US10376465B2

  公开（公告）日：2019-08-13

  The present invention is directed toward respirable dry powders and particles for systemic delivery of pharmaceutically active agents or delivery to the respiratory tract. The dry powders contain one or more monovalent metal cations (such as Na+), are small and dispersible.

  本发明针对的是用于全身给药或呼吸道给药的可吸入干粉和颗粒。干粉含有一种或多种单价金属阳离子（如 Na+），体积小且可分散。
• Methods for producing respirable dry powders
  申请人：Pulmatrix Operating Company, Inc.

  公开号：US10589039B2

  公开（公告）日：2020-03-17

  The invention related to dry powders that contain a therapeutic agent. The dry powders have characteristics, e.g., they are processable and/or dense in therapeutic agent that provide advantages for formulating and delivering therapeutic agents to patients.

  本发明涉及含有治疗剂的干粉。干粉具有可加工和/或富含治疗剂等特点，这些特点为配制治疗剂和向患者提供治疗剂提供了优势。