2-((4-methoxybenzyl)thio)acetaldehyde | 85301-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-((4-methoxybenzyl)thio)acetaldehyde
• 英文别名: 2-[(4-Methoxyphenyl)methylsulfanyl]acetaldehyde
• CAS: 85301-93-5
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: NTBFCEWNFORPQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.6±25.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((4-methoxybenzyl)thio)acetaldehyde 在 三丁基膦 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 3.5h， 生成 methyl (4R)-3-<2-(4-methoxybenzylthio)ethyl>-2-thioxothiazolidine-4-carboxylate
  参考文献：
  名称：

  Synthesis of Thiazolidine-2-thione Derivatives and Evaluation of Their Hepatoprotective Effects.

  摘要：

  合成了一系列N-(巯基烷基)噻唑烷-2-硫酮及其衍生物，并评估了它们对Propionibacterium acnes脂多糖（P. acnes-LPS）诱导的小鼠肝损伤和体外大鼠肝微粒体脂质过氧化（LPO）形成的肝保护活性。通过N-(对甲氧基苄硫基烷基)半胱氨酸甲酯（11）与1,1'-硫代羰基二咪唑反应，随后去保护，得到了相应的噻唑烷-2-硫酮衍生物。在合成的化合物中，1a和2a显示出最强的抗P. acnes-LPS诱导的肝损伤的肝保护活性。化合物1a-f和4抑制了体外LPO的形成。选择化合物1a和2a进行进一步的药理学评估。

  DOI：

  10.1248/cpb.41.876
• 作为产物：
  描述：

  (2,2-diethoxyethyl)(4-methoxybenzyl)sulfane 在 三氯乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 2-((4-methoxybenzyl)thio)acetaldehyde
  参考文献：
  名称：

  5,6-二氢-2,3-双芳基-8 H-咪唑并[ 2,1- c ] [1,4]噻嗪的新型合成

  摘要：

  由相应的2-硫代甲基咪唑制备双芳基-8 H-咪唑并[ 2，1- c ] [1，4]噻嗪。基于苯甲醚与受保护的2-硫代乙醛的缩合反应，提出了一种新颖高效的中间体中间体。

  DOI：

  10.1002/jhet.5570190623

文献信息

• Synthesis of Boronocysteine
  作者：Tom Sheppard、Samantha Gibson、Derek Macmillan

  DOI：10.1055/s-0036-1591491

  日期：2018.2

  Herein we report the first synthesis of protected boronocysteine. The target compound was prepared via copper-catalysed diastereoselective nucleophilic borylation of a sulfinimine. After deprotection to give the amine as the hydrochloride salt, four boronocysteine amide derivatives were prepared through reaction with a variety of different active acylating agents.

  我们在此报告了首次合成受保护的硼半胱氨酸。目标化合物是通过铜催化的立体选择性亲核硼化合成的。在去保护后以盐酸盐的形式得到胺之后，通过与各种不同活性酰化试剂反应制备了四种硼半胱氨酸酰胺衍生物。
• Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogs of bestatin
  作者：E. M. Gordon、J. D. Godfrey、N. G. Delaney、M. M. Asaad、D. Von Langen、D. W. Cushman

  DOI：10.1021/jm00119a023

  日期：1988.11

  Investigations were directed toward inhibition of an aminopeptidase, isolated from rat brain, which has been implicated in the metabolic inactivation of enkephalins. The design rationale and synthesis of novel peptidyl diamino thiol inhibitors of rat brain aminopeptidase are presented, along with accompanying structure-activity analysis. Some of the reported compounds are highly active aminopeptidase inhibitors and possess enzyme inhibitory potency in the nanomolar range (62; I50 = 1 nM). Analysis of the data permits speculations on possible modes of binding of diamino thiols to aminopeptidase. Other investigations were directed toward understanding the mode of enzyme binding of the naturally occurring aminopeptidase inhibitor bestatin. On the basis of published models of enzyme binding, replacement of the C-2 hydroxyl group of bestatin by a sulfhydryl group was anticipated to lead to enhanced inhibition due to a strengthened interaction of this group with enzymic zinc. Contrary to expectations, "thiobestatin" inhibited rat brain aminopeptidase with only the same degree of effectiveness as the corresponding alcohol. Speculations on the possible mode of enzyme-inhibitor binding of bestatin are offered.
• Bioresponsive Small Molecule Polyamines as Noncytotoxic Alternative to Polyethylenimine
  作者：Christopher R. Drake、Abderrahim Aissaoui、Orestis Argyros、James M. Serginson、Bryn D. Monnery、Maya Thanou、Joachim H. G. Steinke、Andrew D. Miller

  DOI：10.1021/mp9002249

  日期：2010.12.6

  Nonviral gene therapy continues to require novel synthetic vectors to deliver therapeutic nucleic acids effectively and safely. The majority of synthetic nonviral vectors employed in clinical trials to date have been cationic liposomes; however, cationic polymers are attracting increasing attention. One of the few cationic polymers to enter clinical trials has been polyethylenimine (PEI); however, doubts remain over its cytotoxicity, and in addition it displays lower levels of transfection than viral systems. Herein, we report on the development of a series of small molecule analogues of PEI that are bioresponsive to the presence of pDNA, forming poly(disulfide)s that are capable of efficacious transfection with no associated toxicity. The most effective small molecule developed, a cyclic disulfide based upon a spermine backbone, is shown to form very well-defined polyplexes (100-200 nm in diameter) that mediate murine lung transfection in vivo to within an order of magnitude of in vivo jetPEI, and at the same time display a much improved cytotoxicity profile.
• LANTOS, I.;RAZGAITIS, C.;SUTTON, B. M., J. HETEROCYCL. CHEM., 1982, 19, N 6, 1375-1376
  作者：LANTOS, I.、RAZGAITIS, C.、SUTTON, B. M.

  DOI：——

  日期：——
• GORDON, E. M.;GODFREY, J. D.;DELANEY, N. G.;ASAAD, M. M.;VON, LANGEN D.;C+, J. MED. CHEM., 31,(1988) N 11, C. 2199-2211
  作者：GORDON, E. M.、GODFREY, J. D.、DELANEY, N. G.、ASAAD, M. M.、VON, LANGEN D.、C+

  DOI：——

  日期：——