4-iodobenzyl thioalcohol | 444010-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-iodobenzyl thioalcohol
• 英文别名: (4-iodophenyl)methanethiol；4-iodobenzyl mercaptan；4-thiomethyliodobenzene；p-iodobenzyl thiol
• CAS: 444010-60-0
• 化学式: C₇H₇IS
• 分子量: 250.103
• InChiKey: OIMBYDFUXNAJSV-UHFFFAOYSA-N

物化性质

• 熔点：
  38 °C(Solv: methanol (67-56-1))
• 沸点：
  265.9±15.0 °C(Predicted)
• 密度：
  1.762±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-iodobenzyl thioalcohol 在 哌啶 、 potassium carbonate 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 diethyl 2-(2-((4-iodobenzyl)thio)benzylidene)malonate
  参考文献：
  名称：

  BF3 介导的 [1,5]-氢化物位移触发环化：硫醚加入游戏

  摘要：

  1,5-氢化物位移触发了 2-(2-(苄硫基)亚苄基)丙二酸酯环化为硫杂色烷，这是首次提出的。三氟化硼作为反应促进剂是这种 C-H 活化成功的关键。量子化学计算表明，所研究的反应是通过O-BF 2 -O 螯合物进行的，这已通过 NMR 分析得到证实。

  DOI：

  10.1002/ejoc.202200547
• 作为产物：
  描述：

  thioacetic acid S-(4-iodobenzyl) ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-iodobenzyl thioalcohol
  参考文献：
  名称：

  Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

  摘要：

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.002

文献信息

• [EN] NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS; PROCESS FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE IV, PROCEDE DE PREPARATION DE CES INHIBITEURS ET COMPOSITIONS CONTENANT CES INHIBITEURS
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2006011035A1

  公开（公告）日：2006-02-02

  The present invention relates to novel organic compounds, more particularly, novel Dipeptidyl peptidase IV (DPP-IV) inhibitors of general formula (I) wherein: Y is -S(O)m-, -CH2-, -CHF-, or -CF2; X and Z are independently -C(=O)-, -NR3-, - O- or -S(O)m-; each occurrence of m is independently 0, 1 or 2; a is 0, 1 or 2; b is 0, 1 or 2; the dotted line [----] in the carbocyclic ring represents an optional double bond; R1 is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl, or substituted or unsubstituted heteroarylalkyl; R2 is hydrogene, nitrile (-CN), COOH, or an isostere of carboxylic; or analogs, tautomers, enantiomers, diastereomers, regioisomers, stereoisomers, polymorphs, pharmaceutically acceptable salts, N-oxides, pharmaceutically acceptable solvates and pharmaceutical compositions containing them.

  该发明涉及新型有机化合物，更特别地，一般式（I）的新型二肽基肽酶IV（DPP-IV）抑制剂，其中：Y为-S(O)m-，-CH2-，-CHF-或-CF2；X和Z独立地为-C(=O)-，-NR3-，-O-或-S(O)m-；m的每次出现独立地为0，1或2；a为0，1或2；b为0，1或2；在碳环中的虚线[----]表示一个可选的双键；R1为取代或未取代的烷基，取代或未取代的烯基，取代或未取代的炔基，取代或未取代的环烷基，取代或未取代的环烷基烷基，取代或未取代的环烯基，取代或未取代的芳基，取代或未取代的芳基烷基，取代或未取代的杂芳基，取代或未取代的杂环烷基，或取代或未取代的杂芳基烷基；R2为氢，腈（-CN），COOH，或羧基的同分异构体；或其类似物，互变异构体，对映异构体，非对映异构体，位置异构体，立体异构体，多晶型，药学上可接受的盐，N-氧化物，药学上可接受的溶剂化合物和含有它们的药物组合物。
• Iodinated thiolcarbonates and method for use as radiographic contrast
  申请人：Alcon Laboratories, Inc.

  公开号：US04125554A1

  公开（公告）日：1978-11-14

  Iodinated thiolcarbonates and a method for using the same as radiographic contrast agents in connection with such X-ray techniques as myleography, lymphography, hysterosalpingography, bronchography and sialography. The general formula of such iodonated thiolcarbonate compounds may be characterized as ##STR1## wherein R represents an iodinated phenyl linked to the sulfur through a lower alkylene group consisting of a straight or branched chain having from 1 to 5 carbon atoms and R.sub.1 is a lower alkyl group consisting of a straight or branched chain having from 1 to 10 carbon atoms.

  碘化巯基碳酸酯及其在脊髓造影、淋巴造影、子宫输卵管造影、支气管造影和唾液管造影等X射线技术中用作放射造影剂的方法。这种碘化巯基碳酸酯化合物的一般结构式可表示为##STR1##其中R代表通过由1至5个碳原子组成的直链或支链低碳烷基团连接到硫的碘化苯基，R.sub.1是由1至10个碳原子组成的直链或支链低烷基团。
• Ferrocenyl Oligo(phenylene‐vinylene) Thiols for the Construction of Self‐Assembled Monolayers
  作者：Christian Amatore、Stephen Gazard、Emmanuel Maisonhaute、Cécile Pebay、Bernd Schöllhorn、Jean‐Laurent Syssa‐Magalé、Jay Wadhawan

  DOI：10.1002/ejic.200700266

  日期：2007.9

  efficient preparation of conjugated oligo(phenylene-ethylene) thiols bearing redox-active ferrocene moieties is described. While minimising the number of synthetic steps, the proposed strategy permits the development of sets of oligomers with varying chain length. The redox properties of the compounds in solution are determined. Preliminary studies of self-assembled monolayers (SAMs) on gold electrodes are

  描述了带有氧化还原活性二茂铁部分的共轭低聚（亚苯基-亚乙基）硫醇的简短而有效的制备。在尽量减少合成步骤数量的同时，所提出的策略允许开发具有不同链长的低聚物组。测定溶液中化合物的氧化还原特性。讨论了金电极上自组装单层 (SAM) 的初步研究，表明通过 SAM 的电子转移确实很快。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Z-styryl sulfone anticancer agents
  申请人：Temple University - Of the Commonwealth System of Higher Education

  公开号：US06576675B1

  公开（公告）日：2003-06-10

  (Z)-styryl benzylsulfones of formula I are useful as anticancer agents: wherein R1 is selected from the group consisting of hydrogen, chloro and nitro; R2 is selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, chloro, bromo, iodo and fluoro; and R3 and R4 are independently selected from the group consisting of hydrogen, lower alkyl, nitro, chloro, bromo, iodo and fluoro; provided that at least one of R1 or R2 is hydrogen. The corresponding (Z)-styryl benzylsulfides are useful as intermediates in the preparation of the biologically active (Z)-styryl benzyl sulfones.

  式I的(Z)-苯乙烯基苯基磺酮是作为抗癌剂有用的化合物，其中：R1选自氢、氯和硝基的群体；R2选自氢、较低的烷基、较低的烷氧基、氯、溴、碘和氟的群体；R3和R4独立地选自氢、较低的烷基、硝基、氯、溴、碘和氟的群体；但要求至少R1和R2中的一个是氢。相应的(Z)-苯乙烯基苯基硫醚是制备具有生物活性的(Z)-苯乙烯基苯基磺酮的中间体。
• N‐Heterocyclic Carbene Mediated Sulfur Extrusion of Disulfides
  作者：Alexander P. Galow、Frank Rominger、Michael Mastalerz

  DOI：10.1002/ejoc.202201383

  日期：2023.2.13

  N-heterocyclic carbenes can be used to substitute the highly carcinogenic aminophosphines to extrude sulfur from disulfides from thioethers (here R=aryl). Furthermore, pharmaceutically more interesting compounds such as cystine can be transformed to lanthionine.

  N-杂环卡宾可用于替代高度致癌的氨基膦，以从硫醚（此处 R = 芳基）的二硫化物中挤出硫。此外，药学上更有趣的化合物如胱氨酸可以转化为羊毛硫氨酸。