4-氯-2,3-二氢-2-氧代-5-噻唑甲醛 | 55359-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氯-2,3-二氢-2-氧代-5-噻唑甲醛
• 英文名称: 4-chloro-2-oxo-2,3-dihydrothiazole-5-carbaldehyde
• 英文别名: 2,4-chloro-5-formyl-2-thiazolinone；4-chloro-2-oxo-3H-1,3-thiazole-5-carbaldehyde
• CAS: 55359-96-1
• 化学式: C₄H₂ClNO₂S
• mdl: MFCD00594925
• 分子量: 163.584
• InChiKey: JRJVASOIWDZPCZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  4-氯-2,3-二氢-2-氧代-5-噻唑甲醛 在 盐酸羟胺 、 碳酸氢钠 作用下， 生成 4-chloro-5-formylthiazole-2(3H)-one oxime
  参考文献：
  名称：

  Azoles。第10部分。噻唑并[4'，5'，4,5]噻吩并[3,2- d ]嘧啶，一种新的杂环系统

  摘要：

  通过使4-氯噻唑-5-甲醛或4-氯噻唑-5-腈与2-巯基乙酸乙酯或2-巯基乙酰胺反应来制备噻吩并[2,3- d ]噻唑。将获得的6-氨基噻吩并[2,3- d ]噻唑-5-羧酰胺转化为相应的噻唑并[4'，5'; 4,5]噻吩并[3,2 - d ]嘧啶-5（6 H）-一种通过在乙酸酐中用原甲酸三乙酯处理。用磷酰氯得到5-氯衍生物，当其与各种胺反应时，该氯原子被氯原子取代。5-氯噻唑并[4'，5'; 4,5]噻吩并[3,2- d ]-嘧啶的还原脱氯反应得到母体杂环。

  DOI：

  10.1016/s0040-4020(01)90380-1
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以62%的产率得到4-氯-2,3-二氢-2-氧代-5-噻唑甲醛
  参考文献：
  名称：

  ANA975的发现：TLR-7激动剂isatoribine的口服前药。

  摘要：

  ANA975是一种5-氨基-3-β-D-呋喃呋喃糖基-3H-噻唑并[4,5-d]嘧啶-2-一衍生物，其合成是寻找一种小分子收费类似的伊沙托立宾的口服前药受体7（TLR-7）激动剂。研究了几种策略以实现ANA975的公斤级合成。描述了三个一般的总合成。在针对丙型肝炎病毒（HCV）的ANA975的I期临床研究中，血浆中快速转化为isatoribine的效果是提供与临床相关的isatoribine水平。

  DOI：

  10.1080/15257770701490472

文献信息

• 3-B-D-ribofuranosylthiazolo [4,5-d] pyridimine nucleosides and uses thereof
  申请人：Averett R. Devron

  公开号：US20050070556A1

  公开（公告）日：2005-03-31

  The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  这项发明涉及3-β-D-核糖呋喃基噻唑并[4,5-d]吡啶嘧啶核苷及含有这种化合物的具有免疫调节活性的药物组合物。该发明还涉及这种化合物和组合物的治疗或预防用途，以及通过给予这种化合物的有效量来治疗本文描述的疾病和紊乱的方法。
• [EN] 3-beta-D-RIBOFURANOSYLTHIAZOLO[4,5-d]PYRIDIMINE NUCLEOSIDES AND USES THEREOF<br/>[FR] NUCLEOSIDES 3-20051222WO03045968A1ANADYS PHARMACEUTICALS INC [US]20030605WX1-20XUS5041426AROBINS ROLAND K [US], et al19910820compounds 6,7,41,42X1,2,12XWO03045968A1ANADYS PHARMACEUTICALS INC [US]20030605"Remington's Pharmaceutical Sciences"Remington's Pharmaceutical SciencesBARANOV ET AL., CHEM. HET. COMPOUNDS, vol. 11, 1975, pages 73BARANOV ET AL.CHEM. HET. COMPOUNDS19751173
  申请人：ANADYS PHARMACEUTICALS INC

  公开号：WO2005121162A1

  公开（公告）日：2005-12-22

  The invention is directed to 3-ß-D-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  本发明涉及3-ß-D-核糖呋喃噻唑[4,5-d]吡啶嘧啶核苷和含有此类化合物的药物组合物，具有免疫调节活性。本发明还涉及这类化合物和组合物的治疗或预防用途，以及通过给予这类化合物的有效剂量来治疗本文所述的疾病和疾病的方法。
• First Synthesis of Novel Aminophenyl Pyridinium-5-(hydroxybenzoyl)-hydrazonomethyl-2-oxothiazol-3-ide Derivatives and Evaluation of Their Anticancer Activities
  作者：Dongguk Min、Moon Hi Han、Seulki Lee、Mankil Jung

  DOI：10.1248/cpb.c15-00441

  日期：——

  The first total synthesis for large-scale production and anticancer activity of novel aminophenylpyridinium-5-(hydroxybenzoyl)hydrazonomethyl-2-oxothiazol-3-ide (PBHT) (1) and its derivatives are reported. The chemical structure of PBHT was unambiguously determined by utilization of the two-dimensional nuclear Overhauser effect (NOE) technique. The anticancer activity against human colon adenocarcinoma (HCT15) cells of all synthesized compounds was approximately four-fold greater than that of 5-fluorouracil, with IC50 values ranging from 10.1 to 14.2 µM. The three structural determinants of hydroxybenzoyl, hydrazinylidene, and pyridinium oxothiazole in the synthesized compounds could be indispensable for exhibiting anticancer activity.

  本研究首次报道了新型氨基苯基吡啶鎓-5-（羟基苯甲酰基）肼甲基-2-氧代噻唑-3-ide (PBHT)（1）及其衍生物的全合成大规模生产和抗癌活性。通过利用二维核欧豪瑟效应（NOE）技术，明确确定了 PBHT 的化学结构。所有合成化合物对人结肠腺癌（HCT15）细胞的抗癌活性约为 5-氟尿嘧啶的四倍，IC50 值为 10.1 至 14.2 µM。合成化合物中的羟基苯甲酰基、亚肼基和吡啶氧噻唑这三种结构决定因素可能是发挥抗癌活性不可或缺的因素。
• 2,4-Dichloro-5-thiazolecarboxaldehyde and a process for its preparation
  申请人：Bayer Aktiengesellschaft

  公开号：US04555577A1

  公开（公告）日：1985-11-26

  The new 2,4-dichloro-5-thiazolecarboxaldehyde of the formula ##STR1## can be prepared in good yields by reacting 2,4-thiazolidinedione (III) with 1-1.5 mol of dimethylformamide and 3-10 mol of phosphorus oxychloride at the reflux temperature of the reaction mixture (about 115.degree. C.) until evolution of HCl gas has ended, and then working up hydrolytically. The aldehyde (II) can readily be converted, via the new oxime (IV), into the corresponding nitrile, 2,4-dichloro-5-cyanothiazole (V), which is a known intermediate for the preparation of herbicidal active compounds of the thiazolyloxyacetamide type.

  公式为##STR1##的新2,4-二氯-5-噻唑羧醛可以通过将2,4-噻唑烷二酮（III）与1-1.5摩尔二甲基甲酰胺和3-10摩尔氧化亚磷酰在反应混合物的沸点（约115℃）下反应，直到HCl气体的产生结束，然后进行水解反应，可以得到良好的产率。醛（II）可以通过新的肟（IV）转化为相应的腈，2,4-二氯-5-氰基噻唑（V），这是制备噻唑氧乙酰胺类除草剂活性化合物的已知中间体。
• 3-Beta-D-Ribofuranosylthiazolo&lsqb; 4,5-D&rsqb; Pyridimine Nucleosides and Uses Thereof
  申请人：Averett Devron R.

  公开号：US20080070852A1

  公开（公告）日：2008-03-20

  The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

  本发明涉及3-β-D-核糖呋喃基噻唑[4,5-d]嘧啶核苷及含有这种化合物的药物组合物，其具有免疫调节活性。本发明还涉及使用这种化合物和组合物进行治疗或预防，以及通过给予有效剂量的这种化合物来治疗本文所述的疾病和障碍的方法。