5-anilinomethylidene-3-etylrhodanine | 118050-10-5

• 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: 5-anilinomethylidene-3-etylrhodanine
• 英文别名: 5-(Z)-anilinomethylene-3-ethyl-2-thioxo-thiazolidin-4-one；(5Z)-5-(anilinomethylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 118050-10-5
• 化学式: C₁₂H₁₂N₂OS₂
• 分子量: 264.372
• InChiKey: PXBJDLPPRXOBIZ-NTMALXAHSA-N

物化性质

• 沸点：
  366.0±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-anilinomethylidene-3-etylrhodanine 在 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.5h， 生成 2-[3-Ethyl-5-[2-[3-ethyl-thiazolidin-(2Z)-ylidene]-eth-(Z)-ylidene]-4-oxo-thiazolidin-(2Z)-ylidenemethyl]-3-methyl-naphtho[2,1-d]thiazol-3-ium; iodide
  参考文献：
  名称：

  Structure−Activity of Novel Rhodacyanine Dyes as Antitumor Agents

  摘要：

  We have previously reported that rhodacyanine dyes, such as 1 and 2, exhibited a potent inhibitory effect on the growth of several tumor cells and that 4-oxothiazolidine (rhodanine) was an essential moiety for antitumor activity. On the basis of our foregoing work, two types of rhodacyanine dyes, which categorized into class I and II depending on the methine length, were synthesized and evaluated as a novel antitumor agent. Attention was particularly focused on the structure-activity study of two heteroaromatic rings. In class I, where the A rings were conjugated to rhodanine via two methine groups, compounds 1, 20, 23, and 24 were found to be efficacious in tumor-bearing nude mice model study, but they did not have the chemical properties (stability, solubility) suitable for clinical use. In contrast, in class II, where the A rings were directly conjugated to rhodanine, compounds 13 and 25, which possessed a benzothiazole moiety for the A ring, exhibited the favarable biological and chemical properties. Therefore, we decided to have a benzothiazole moiety as the A ring and introduce various heterocyclic groups for the B ring. As a result, the pyridinium ring was selected as the optimal moiety for the B ring (compound 13). Further, the variation of counteranion had a profound effect on solubility in water without influence on antitumor activity. Chloride anion was selected as the favorable anion with respect to synthetic method as well as solubilty in water. Our study finally led us to the identification of compound 3 (MKT 077, 1-ethyl-2-[[3-ethyl-5-(methylbenzothiazolin-2-ylidene)-4-oxothiazolidin-2-ylidene]methyl]pyridinium chloride) as the candidate for clinical trials and is currently subjected to further investigation as a potent antitumor agent in phase I clinical trial for the treatment of solid tumors.

  DOI：

  10.1021/jm970590k
• 作为产物：
  描述：

  3-乙基-2-硫代-4-噻唑烷二酮 、 N,N'-二苯甲脒 以 Petroleum ether 为溶剂， 反应 1.0h， 生成 5-anilinomethylidene-3-etylrhodanine
  参考文献：
  名称：

  具有抗肿瘤活性的新型若丹菁染料的合成与评价。

  摘要：

  合成了若丹菁染料和几种类似的离域亲脂性阳离子（DLC），并将其评估为新型抗肿瘤剂。罗丹菁染料由两个杂芳族环组成，例如在共轭体系两个末端的噻唑和中间的4-氧噻唑烷（若丹宁）。发现具有这种独特双共轭结构的化合物可抑制几种肿瘤细胞系（例如结肠癌CX-1）的生长，并且对正常肾细胞系CV-1的毒性相对较低（例如，IC50（CX- 1）= 50 nM，IC50（CV-1）= 17.3 microM；对于化合物5）的选择性指数= 346。还发现这些化合物在荷瘤裸鼠模型中是有效的（例如，针对人黑素瘤LOX；化合物5的T / C（％）＝ 168）。罗丹菁的结构修饰，包括删除涉及花青素共轭体系的杂芳环，并用结构上相关的部分（例如4-氧代咪唑烷或4-氧代-1,3-二硫杂环戊烷）取代若丹宁，会导致选择性和/或活性损失。我们目前的结构活性研究表明，具有罗丹宁部分的双共轭体系对于罗丹菁染料的选择性活性至关重要，我们发

  DOI：

  10.1021/jm9702692

文献信息

• Synthesis and Evaluation of Novel Rhodacyanine Dyes That Exhibit Antitumor Activity
  作者：Masayuki Kawakami、Keizo Koya、Toshinao Ukai、Noriaki Tatsuta、Akihiko Ikegawa、Keizo Ogawa、Tadao Shishido、Lan Bo Chen

  DOI：10.1021/jm9702692

  日期：1997.9.1

  synthesized and evaluated as novel antitumor agents. Rhodacyanine dye consists of two heteroaromatic rings such as thiazoles at both termini of the conjugate systems and 4-oxothiazolidine (rhodanine) in the middle of it. Compounds with such a unique double-conjugate structure were found to inhibit the growth of several tumor cell lines, such as colon carcinoma CX-1, and to exhibit relatively low toxicity against

  合成了若丹菁染料和几种类似的离域亲脂性阳离子（DLC），并将其评估为新型抗肿瘤剂。罗丹菁染料由两个杂芳族环组成，例如在共轭体系两个末端的噻唑和中间的4-氧噻唑烷（若丹宁）。发现具有这种独特双共轭结构的化合物可抑制几种肿瘤细胞系（例如结肠癌CX-1）的生长，并且对正常肾细胞系CV-1的毒性相对较低（例如，IC50（CX- 1）= 50 nM，IC50（CV-1）= 17.3 microM；对于化合物5）的选择性指数= 346。还发现这些化合物在荷瘤裸鼠模型中是有效的（例如，针对人黑素瘤LOX；化合物5的T / C（％）＝ 168）。罗丹菁的结构修饰，包括删除涉及花青素共轭体系的杂芳环，并用结构上相关的部分（例如4-氧代咪唑烷或4-氧代-1,3-二硫杂环戊烷）取代若丹宁，会导致选择性和/或活性损失。我们目前的结构活性研究表明，具有罗丹宁部分的双共轭体系对于罗丹菁染料的选择性活性至关重要，我们发
• A simple, novel method for the preparation of polymer-tetherable, zwitterionic merocyanine NLO-chromophores
  作者：A. J. Kay、A. D. Woolhouse、G. J. Gainsford、T. G. Haskell、T. H. Barnes、I. T. McKinnie、C. P. Wyss

  DOI：10.1039/b008316j

  日期：——

  A suite of polymer-ready nonlinear optical merocyanines has been synthesised and characterised. The tethering functionality—a vicinal dihydroxypropyl residue—is introduced onto the donor nitrogen of the chromophore precursor without the need for protection/deprotection steps, thereby giving ready access to potentially high Tg condensation polymer systems. An X-ray crystal structure determination on a representative chromophore 5 confirms the largely zwitterionic nature of these systems and experimental measurements of second-order nonlinear response [β(0)], by hyper-Raleigh scattering, indicate that a pyridylidene donor–quinomethide acceptor combination gives rise to the largest nonlinearity.

  一套聚合物就绪的非线性光学部花青已被开发出来 合成并表征。网络共享功能——邻域 二羟丙基残基——被引入到供体氮上 发色团前体，无需保护/脱保护步骤， 从而可以随时获得潜在的高 Tg 冷凝 聚合物系统。代表性物质的 X 射线晶体结构测定 发色团 5 证实了很大程度上 这些系统的两性离子性质和二阶实验测量 非线性响应 [β(0)]，作者：hyper-Raleigh 散射，表明吡啶基供体-喹诺酮受体 组合产生最大的非线性。
• Kovtunenko, V. A.; Tyltin, A. K.; Turov, A. V., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 5.2, p. 972 - 977
  作者：Kovtunenko, V. A.、Tyltin, A. K.、Turov, A. V.、Babichev, F. S.

  DOI：——

  日期：——
• KOVTUNENKO, V. A.;TYLTIN, A. K.;TUROV, A. V.;BABICHEV, F. S., ZH. ORGAN. XIMII, 25,(1989) N, S. 1080-1085
  作者：KOVTUNENKO, V. A.、TYLTIN, A. K.、TUROV, A. V.、BABICHEV, F. S.

  DOI：——

  日期：——
• KLEBANOV, B. M.;MIKITENKO, E. K.;MOGILEVICH, S. E.;ROMANOV, N. N.
  作者：KLEBANOV, B. M.、MIKITENKO, E. K.、MOGILEVICH, S. E.、ROMANOV, N. N.

  DOI：——

  日期：——