5-[2-(3-ethyl-2-benzothiazolylidene)-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone | 60884-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-[2-(3-ethyl-2-benzothiazolylidene)-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone
• 英文别名: 3-ethyl-5-<2-(3-ethylbenzothiazolin-2-ylidene)ethylidene>rhodanine；4-thiazolidinone, 3-ethyl-5-[2-(3-ethyl-2(3H)-benzothiazolylidene)ethylidene]-2-thioxo-；(5Z)-3-ethyl-5-[(2Z)-2-(3-ethyl-1,3-benzothiazol-2-ylidene)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 60884-76-6
• 化学式: C₁₆H₁₆N₂OS₃
• 分子量: 348.514
• InChiKey: KJXKJGBRCAUHMN-FOIMCPNXSA-N

物化性质

• 沸点：
  413.8±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[2-(3-ethyl-2-benzothiazolylidene)-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone 以 环己烷 为溶剂， 生成 5-[2-(3-Ethylbenzthiazolinyliden-(2))-ethyliden]-3-ethyl-rhodanin
  参考文献：
  名称：

  Conformational analysis and photoisomerization of merocyanine dyes studied by visible absorption, resonance Raman and IR spectroscopies

  摘要：

  The photoisomerization of the merocyanine dyes, 5-[2-(3-ethyl-2-benzothiazolylidene)-1-methyl-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone (Et(Me)MD) and 5-[2-(3-ethyl-2-benzothiazolylidene)ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone (EtMD), in solution was studied by visible absorption, resonance Raman and IR spectroscopies. It was found that the most stable conformers for Et(Me)MD and EtMD of the four possible isomers A-D were different. For Et(Me)MD, isomer A, which was stable in cyclohexane and carbon tetrachloride, was photoisomerized to isomer C by 514.5 nm laser irradiation, Isomer C returned to isomer A slowly in the dark or rapidly on 488.0 nm laser irradiation. In contrast, Isomer C for EtMD, which was stable in the solvents, was photoisomerized to isomer A by 488.0 or 457.9 nm laser irradiation. Isomer A returned to isomer C slowly in the dark or rapidly on 514.5 nm laser irradiation in cyclohexane. Possible photoisomerization mechanisms are discussed based on the rotational motions around the two C=C double bonds of the central conjugated system. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s0022-2860(96)09448-3
• 作为产物：
  描述：

  5-anilinomethylidene-3-etylrhodanine 在 乙酸酐 、 三乙胺 作用下， 反应 5.5h， 生成 5-[2-(3-ethyl-2-benzothiazolylidene)-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone
  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

• SLOMINSKIJ YU. L.; TOLMACHEV A. I.; SHULEZHKO L. M., UKR. XIM. ZH. <UKZN-A4>, 1975, 41, HO 3, 284-286
  作者：SLOMINSKIJ YU. L.、 TOLMACHEV A. I.、 SHULEZHKO L. M.

  DOI：——

  日期：——
• LYUBICH M. S.; SYTNIK Z. P.; KUDRYAVSKAYA N. V., XIMIYA GETEROTSIKL. SOEDIN., 1977, HO 9,
  作者：LYUBICH M. S.、 SYTNIK Z. P.、 KUDRYAVSKAYA N. V.

  DOI：——

  日期：——
• 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
• Conformational analysis and photoisomerization of merocyanine dyes studied by visible absorption, resonance Raman and IR spectroscopies
  作者：Masao Takayanagi、Munetaka Nakata、Yukihiro Ozaki、Keiji Iriyama、Mitsuo Tasumi

  DOI：10.1016/s0022-2860(96)09448-3

  日期：1997.3

  The photoisomerization of the merocyanine dyes, 5-[2-(3-ethyl-2-benzothiazolylidene)-1-methyl-ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone (Et(Me)MD) and 5-[2-(3-ethyl-2-benzothiazolylidene)ethylidene]-3-ethyl-2-thioxo-4-thiazolidinone (EtMD), in solution was studied by visible absorption, resonance Raman and IR spectroscopies. It was found that the most stable conformers for Et(Me)MD and EtMD of the four possible isomers A-D were different. For Et(Me)MD, isomer A, which was stable in cyclohexane and carbon tetrachloride, was photoisomerized to isomer C by 514.5 nm laser irradiation, Isomer C returned to isomer A slowly in the dark or rapidly on 488.0 nm laser irradiation. In contrast, Isomer C for EtMD, which was stable in the solvents, was photoisomerized to isomer A by 488.0 or 457.9 nm laser irradiation. Isomer A returned to isomer C slowly in the dark or rapidly on 514.5 nm laser irradiation in cyclohexane. Possible photoisomerization mechanisms are discussed based on the rotational motions around the two C=C double bonds of the central conjugated system. (C) 1997 Elsevier Science B.V.