2-<<(4-methoxyphenyl)methyl>thio>ethanol | 35378-93-9

• 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-methoxyphenyl)methyl>thio>ethanol
• 英文别名: 4-methoxybenzyl 2-hydroxyethyl monosulfide；2-(4-methoxybenzylthio)ethanol；2-(p-methoxybenzylthio)ethanol；β-Hydroxyaethyl-p-methoxybenzyl-thioaether；2-{[(4-Methoxyphenyl)methyl]sulfanyl}ethan-1-ol；2-[(4-methoxyphenyl)methylsulfanyl]ethanol
• CAS: 35378-93-9
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: AOJDHGMFDUEVML-UHFFFAOYSA-N

物化性质

• 熔点：
  48.9-49.2 °C
• 沸点：
  339.8±22.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<<(4-methoxyphenyl)methyl>thio>ethanol 在 三氧化硫吡啶 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以52%的产率得到2-((4-methoxybenzyl)thio)acetaldehyde
  参考文献：
  名称：

  Bioresponsive Small Molecule Polyamines as Noncytotoxic Alternative to Polyethylenimine

  摘要：

  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.

  DOI：

  10.1021/mp9002249
• 作为产物：
  描述：

  4-甲氧基氯苄 、 2-巯基乙醇 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到2-<<(4-methoxyphenyl)methyl>thio>ethanol
  参考文献：
  名称：

  Bioresponsive Small Molecule Polyamines as Noncytotoxic Alternative to Polyethylenimine

  摘要：

  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.

  DOI：

  10.1021/mp9002249

文献信息

• Thiol ligands and complexes for X-ray imaging
  申请人：Mallinckrodt Medical, Inc.

  公开号：US05616312A1

  公开（公告）日：1997-04-01

  The present invention provides new and structurally diverse compositions comprising compounds of the general formula: ##STR1## Wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are the same or different and are --CO--(CH.sub.2).sub.y --SH, --(CH.sub.2).sub.2 --SH, --SO.sub.2 --(SH.sub.2).sub.t --SH,--SH,--(CH.sub.2).sub.q --COOH, and --(CH.sub.2).sub.v --CONR.sup.6 R.sup.7, provided at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is a sulfur containing moiety; n is 0 to about 10; i is 2 to about 5; j is 2 to about 5; y is 1 to about 5; z is 1 to about 6; t is 1 to about 5; q is 1 to about 5; v is 1 to about 5; R.sup.6 is H, alkyl, hydroxyalkyl, polyhydroxyalkyl, arylalkyl or alkoxyalkyl; R.sup.7 is H, alkyl, hydroxyalkyl, polyhydroxyalkyl, arylalkyl or alkoxyalkyl; and R.sup.7 can be polyamine when R.sup.6 is H. Methods for imaging using compositions of the invention are also provided.

  本发明提供了新的结构多样的组合物，包括符合以下一般式的化合物：##STR1## 其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5相同或不同，分别为--CO--(CH.sub.2).sub.y --SH、--(CH.sub.2).sub.2 --SH、--SO.sub.2 --(SH.sub.2).sub.t --SH、--SH、--(CH.sub.2).sub.q --COOH和--(CH.sub.2).sub.v --CONR.sup.6 R.sup.7，至少其中之一为含硫基团；n为0至约10；i为2至约5；j为2至约5；y为1至约5；z为1至约6；t为1至约5；q为1至约5；v为1至约5；R.sup.6为H、烷基、羟基烷基、多羟基烷基、芳基烷基或烷氧基烷基；R.sup.7为H、烷基、羟基烷基、多羟基烷基、芳基烷基或烷氧基烷基；当R.sup.6为H时，R.sup.7可以是多胺。本发明还提供了使用该组合物进行成像的方法。
• ORGANOSULFUR COMPOUNDS AS POTENTIAL FUNGICIDES: THE PREPARATION AND PROPERTIES OF SOME SUBSTITUTED BENZYL 2-HYDROXYETHYL OLIGOSULFIDES
  作者：Ezekiel T. Ayodele、Harry R. Hudson、Isaac A.O. Ojo、Max Pianka

  DOI：10.1080/10426500008043656

  日期：2000.4.1

  Abstract Compounds of the general type ArCH2SnCH2CH2OH (n = 1–4, Ar = Ph. 2-MeC6H4, 4-MeC6H4, 4-ClC6H4, 4-MeOC6H4; n = 1–3, Ar = 2-ClC6H4; n =2 Ar = 4-FC6H4; n =3 or 4, Ar = 2-furyl) have been prepared as analogues of the trisulfide PhCH2SSSCH2CH2OH antimicrobial compound which occurs in the plant Petiveria alliacea) and their potential application as agricultural fungicides has been examined. In vitro

  摘要 一般类型的化合物 ArCH2SnCH2CH2OH (n = 1–4, Ar = Ph. 2-MeC6H4, 4-MeC6H4, 4-ClC6H4, 4-MeOC6H4; n = 1-3, Ar = 2-ClC6H4; n =2 Ar = 4-FC6H4；n = 3 或 4，Ar = 2-呋喃基）已被制备为三硫化物 PhCH2SSSCH2CH2OH 抗菌化合物的类似物，该化合物存在于植物 Petiveria alliacea）中，并且它们作为农用杀菌剂的潜在应用已得到检验。针对小镰刀菌、尖孢镰刀菌和禾本科青霉病菌的体外试验表明，所有化合物在 1000 ppm 时都对这些微生物产生了 > 80% 的控制。100 和 10 ppm 的测试表明控制水平不同，但活性与存在的硫原子数量无关。选定的化合物也被证明在体内对大麦幼苗上的白粉病具有活性，Borrytis fabae 和 Uromyces
• Substituierte Phenoxypropionate
  申请人：NIHON TOKUSHU NOYAKU SEIZO K.K.

  公开号：EP0092112A1

  公开（公告）日：1983-10-26

  Neue substituierte Phenoxypropionate der Formel in der Ar die Gruppe bezeichnet, in der Y für ein Halogen-Atom oder eine Trifluoromethyl-Gruppe und b für 1 oder 2 stehen, R ein Wasserstoff-Atom oder eine Methyl-Gruppe bezeichnet, X ein Wasserstoff-Atom, ein Halogen-Atom, eine Nitro-Gruppe, eine niedere Alkyl-Gruppe oder eine niedere Alkoxy-Gruppe bezeichnet, a und m jeweils für 1 oder 2 stehen und n für 0, 1 oder 2 steht, mehrere Verfahren zur Herstellung der neuen Stoffe und deren Verwendung zur Bekämpfung von Unkräutern. Neue Zwischenprodukte zur Herstellung der Stoffe der Formel (I) sowie Verfahren zur Synthese der neuen Zwischenprodukte.

  新的取代苯氧基丙酸酯，其式中 Ar 表示 Y 表示卤素原子或三氟甲基且 b 表示 1 或 2 的基团，R 表示氢原子或甲基，X 表示氢原子、卤素原子、硝基、低级烷基或低级烷氧基，a 和 m 各表示 1 或 2，n 表示 0、1 或 2。 用于制备式（I）物质的新中间体以及合成新中间体的工艺。
• 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.
• 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：——