3-methoxydithiosalicylic acid | 20557-42-0

• 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: 3-methoxydithiosalicylic acid
• 英文别名: Bis-(2-carbossi-6-metossifenil)disolfuro；3,3'-dimethoxy-2,2'-disulfanediyl-bis-benzoic acid；2-[(2-Carboxy-6-methoxyphenyl)disulfanyl]-3-methoxybenzoic acid
• CAS: 20557-42-0
• 化学式: C₁₆H₁₄O₆S₂
• 分子量: 366.416
• InChiKey: HYGHIGKYEGQBBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-methoxydithiosalicylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2-Mercapto-3-methoxyphenyl)methanol
  参考文献：
  名称：

  卡宾催化获得硫色烯衍生物：通过从二硫化物中缓慢释放硫醇来控制反应途径

  摘要：

  含有二硫键的底物更稳定、气味更小，可用作有机合成中的苯硫酚前体。在此，开发了 α-溴烯醛和 2,2'-二硫代二苯甲醛之间的 N-杂环卡宾 (NHC) 催化反应。通过缓释策略，可以有效抑制副反应，获得收率高、光学纯度高的手性硫色烯衍生物。当探索所需产品在农药开发中的抗菌效用时，应用研究显示出令人鼓舞的结果。

  DOI：

  10.1021/acs.orglett.3c01414
• 作为产物：
  描述：

  2-氨基-3-甲氧基苯甲酸 在 盐酸 、 sodium nitrite 、 sodiumsulfide nonahydrate 、 sulfur 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 3-methoxydithiosalicylic acid
  参考文献：
  名称：

  卡宾催化获得硫色烯衍生物：通过从二硫化物中缓慢释放硫醇来控制反应途径

  摘要：

  含有二硫键的底物更稳定、气味更小，可用作有机合成中的苯硫酚前体。在此，开发了 α-溴烯醛和 2,2'-二硫代二苯甲醛之间的 N-杂环卡宾 (NHC) 催化反应。通过缓释策略，可以有效抑制副反应，获得收率高、光学纯度高的手性硫色烯衍生物。当探索所需产品在农药开发中的抗菌效用时，应用研究显示出令人鼓舞的结果。

  DOI：

  10.1021/acs.orglett.3c01414

文献信息

• Optimization of unique, uncharged thioesters as inhibitors of HIV replication
  作者：Pratibha Srivastava、Marco Schito、Rasem J. Fattah、Toshiaki Hara、Tracy Hartman、Robert W. Buckheit、Jim A. Turpin、John K. Inman、Ettore Appella

  DOI：10.1016/j.bmc.2004.09.032

  日期：2004.12

  A combinatorial chemistry approach was employed to prepare a restricted library of N-substituted S-acyl-2-mercapto-benzamide thioesters. It was shown that many members of this chemotype display anti-HIV activity via their ability to interact with HIV-1, HIV-2, SIV-infected cells, cell-free virus, and chronically and latently infected cells in a manner consistent with targeting of the highly conserved HIV-1 NCp7 zinc fingers. Compounds were initially screened using two different in vitro antiviral assays and evaluated for stability in neutral buffer containing 10% pooled human Serum using a spectrophotometric assay. These data revealed that there was no significant correlation between thioester stability and antiviral activity, however, a slight inverse correlation between serum stability and virucidal activity was noted. Based on the virucidal capability and the ability to select lead compounds to inhibit virus expression from latently infected TNFalpha-induced U1 cells, we next determined if these compounds could prevent HIV cell-to-cell transmission. Several thioesters demonstrated potent inhibition of HIV cell-to-cell transmission with EC50 values in the 80-100 nM range. Thus, we have optimized a series of restricted thioesters and provided evidence that serum stability is not required for antiviral activity. Moreover, selected compounds show potential for development as topical microbicides. (C) 2004 Elsevier Ltd. All rights reserved.
• Ring-hydroxylated analogs of lucanthone as antitumor agents
  作者：Sydney Archer、Kenneth J. Miller、Rabindra Rej、Cecily Periana、Lloyd Fricker

  DOI：10.1021/jm00345a006

  日期：1982.3

  A series of ring-alkoxylated and ring-hydroxylated analogues of lucanthone was prepared and tested for antitumor activity. The most biologically interesting members of this group were the 7-hydroxylucanthone derivatives, 50 and 51, which gave T/C values in the NCI P-388 antitumor screen of 188 and 265, respectively. The apparent association constants and delta Tm values for a number of analogue-DNA complexes were determined to ascertain whether there was any quantitative correlation with biological activity. The most that can be said is that intercalation may be a necessary but far from sufficient condition for antitumor activity.
• Synthesis of a New Allosteric Carrier Containing Three Conformationally Related Subunits
  作者：Ana M. Costero、Miguel Pitarch

  DOI：10.1021/jo00090a010

  日期：1994.6

  A new allosteric carrier was prepared. This compound consists of three crown ether subunits in which conformational information is transferred through two biphenyl systems. This system is able to complex nonionic species in both external crown ether subunits. The allosteric cooperativity in this system was established and its ability to transport Hg(CN)(2) has been studied.
• Vitali; Amoretti; Mossini, Farmaco, Edizione Scientifica, 1968, vol. 23, # 5, p. 468 - 476
  作者：Vitali、Amoretti、Mossini

  DOI：——

  日期：——
• ARYLTHIO COMPOUNDS AS ANTIBACTERIAL AND ANTIVIRAL AGENTS
  申请人：Warner-Lambert Company LLC

  公开号：EP0775110B1

  公开（公告）日：2005-10-05