2'-(2-羟基苯基)-2'-噻唑啉-4'-羧酸 | 49608-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2'-(2-羟基苯基)-2'-噻唑啉-4'-羧酸
• 英文名称: 2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid
• 英文别名: Dihydroaeruginoic acid；2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 49608-51-7
• 化学式: C₁₀H₉NO₃S
• mdl: MFCD01191410
• 分子量: 223.252
• InChiKey: CECDPVOEINSAQG-UHFFFAOYSA-N

物化性质

• 沸点：
  466.3±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜：乙醇；甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-(2-羟基苯基)-2'-噻唑啉-4'-羧酸 在 sodium tetrahydroborate 、 乙酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 aerugine
  参考文献：
  名称：

  Identification of the bacterial metabolite aerugine as potential trigger of human dopaminergic neurodegeneration

  摘要：

  DOI：

  10.1016/j.envint.2023.108229
• 作为产物：
  描述：

  邻羟基苯甲腈 、 L-半胱氨酸 生成 2'-(2-羟基苯基)-2'-噻唑啉-4'-羧酸
  参考文献：
  名称：

  TASIRO, TOMOYASU;SIGEHTOMI, YUDZI;ODZAVA, YASUKO;KATSUMATA, MANABU;UTIDZO+

  摘要：

  DOI：

文献信息

• Thiazoline‐Iridium (III) Complexes and Immobilized Nanomaterials as Selective Catalysts in <i>N</i> ‐Alkylation of Amines with Alcohols
  作者：Serpil Denizaltı、Serkan Dayan、Salih Günnaz、Ertan Şahin

  DOI：10.1002/aoc.5970

  日期：2020.12

  thiazoline‐iridium (III) complexes (4–7) derived from cysteine were prepared and fully characterized by conventional methods. The molecular structure of complex 5 was also determined by single‐crystal X‐ray diffraction. These complexes were evaluated as catalysts for hydrogen‐borrowing reactions of amines with alcohols. In particular, complex 5 showed the best activity as catalyst. Various amines have

  在这项研究中，一个新的系列噻唑啉的铱（III）配合物（4 - 7）来自半胱氨酸制备并通过常规方法充分表征。配合物5的分子结构也通过单晶X射线衍射确定。这些络合物被评估为胺与醇的氢借位反应的催化剂。特别地，配合物5显示出作为催化剂的最佳活性。各种胺已被醇烷基化，可提供中等至良好的收率（33–99％）。此外，采用最佳催化剂5进行超声处理，制备了固定化的纳米材料（M 1,2）。分别使用多壁碳纳米管（MWCNT）和氧化石墨烯（GO），并通过X射线衍射（XRD），傅里叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FE-SEM）进行表征，能量色散X射线（EDX）光谱和电感耦合等离子体质谱（ICP-MS）。的中号1,2纳米材料也进行了测试，如用于模型催化反应的催化剂Ñ烷基化。的中号1的纳米材料显示出比显著更高的活性中号2纳米材料。的中号1催化剂通过过滤回收并用于与高转化率4个催化循环（99％，97％，96％，和86％）再利用。
• A preparative, spectroscopic and equilibrium study of some phenyl-2-thiazoline fluorophores for aluminium(III) detection
  作者：Stephanie G. Lambert、Jo-Anne M. Taylor、Kate L. Wegener、Susan L. Woodhouse、Stephen F. Lincoln、A. David Ward

  DOI：10.1039/b001905o

  日期：——

  As part of a study of fluorophores for selective Al3+ detection and of potential use in the study of intracellular Al3+, the preparative, UV–visible and fluorescence spectroscopic, and Al3+ coordination characteristics of five ligands containing the conjugated phenolic substituted thiazoline chromophore of the natural siderophore, pyochelin, 2-[2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1

  作为用于选择性检测Al 3+的荧光团的研究的一部分，以及在细胞内Al 3+的研究中的潜在用途，五种含有共轭酚取代基的配体的制备，紫外可见光谱和荧光光谱以及Al 3+配位特征天然铁载体的噻唑啉生色团，pyochelin，2- [2-（2-羟基苯基）-4,5-二氢-1,3-噻唑-4-基] -3-甲基-1,3-噻唑烷-4-羧酸酸）1，已报道。五个配体是2-（2-羟基苯基）-4,5-二氢-1,3-噻唑-4-羧酸，2，2-（4,5-二氢-1,3-噻唑-2-基）苯酚，3，4-溴-2-（4,5-二氢-1,3-噻唑-2-基）苯酚，4，2-（4,5-二氢-1,3-噻唑-2-基）-5-硝基苯酚5和2-（4,5-二氢-1,3-噻唑-2-基）-4-硝基苯酚，6。所有形式稳定二元Al 3+在75％甲醇和25％水的情况下的复合物2，和73.2％的甲醇，24.4％水和2.4％ Ñ，Ñ二甲基甲酰胺中的情况下，3 - 6，并表现出显着UV
• In-vitro antiproliferative activity of 4-substituted 2-(2-hydroxyphenyl)thiazolines on murine leukemia cells
  作者：Gary T. Elliott、William A. Nagle、Ken F. Kelly、David McCollough、Robert L. Bona、E. Robert Burns

  DOI：10.1021/jm00125a018

  日期：1989.5

  Two previously synthesized and two structurally novel thiazoline iron chelators are described. N4-Benzyl-N1,N8-bis[[2-(2-hydroxyphenyl)thiazolin-4-yl]carbonyl] homospermidine (5) proved to be the most potent antiproliferative and cytocidal compound in the series with in vitro IC50 values of 3 and 1 microM on L1210 and P388 murine cell lines. The N4-acetyl analogue 7 was considerably less active than

  描述了两种先前合成的和两种结构新颖的噻唑啉铁螯合剂。N4-苄基-N1，N8-双[[2-（2-（2-羟基苯基）噻唑啉-4-基]羰基]高嘧啶（5）被证明是该系列中最有效的抗增殖和杀细胞化合物，其体外IC50值为3在L1210和P388鼠细胞系上为1 microM。N4-乙酰基类似物7的活性明显低于5，其IC50和细胞活力值与结构简单的噻唑啉2和3相似。通过将3和7的抗增殖活性传递到细胞悬液中，可以大大降低或消除它们的活性。与FeCl3的摩尔比为1：1的混合物，而活性5不受Fe（III）螯合的影响。不出所料 3诱导了100 microM的G1 / S细胞周期阻滞，与DNA合成的干扰一致，而10 microM 5则不影响L1210细胞周期的分布。ti化胸腺嘧啶核苷掺入研究证实，在浓度低于40 microM的条件下，有5种不能干扰DNA合成。碱性洗脱研究表明，在10 microM的浓度下5不会在体外
• DESFERRITHIOCIN POLYETHER ANALOGUES AND USES THEREOF
  申请人：Bergeron, JR. Raymond J.

  公开号：US20120184586A1

  公开（公告）日：2012-07-19

  Desferrithiocin analogues represents by the structural formulae described here, such as formula (I), are useful in treating conditions such as metal overload (e.g., iron overload from transfusion therapy), oxidative stress, and neoplastic and preneoplastic conditions.

  Desferrithiocin类似物由此处描述的结构式代表，例如公式（I），在治疗诸如金属过载（例如输血治疗引起的铁过载）、氧化应激以及肿瘤和癌前病变等疾病方面是有用的。
• Stereochemical Assignment of the Pyochelins
  作者：Kenneth L. Rinehart、Andrew L. Staley、Scott R. Wilson、Robert G. Ankenbauer、Charles D. Cox

  DOI：10.1021/jo00114a029

  日期：1995.5

  The synthesis of pyochelin has been much improved but gives four stereoisomers. The stereochemistry of the two naturally occurring pyochelins I and II has been assigned, based on (1) the similarity of the NMR spectra of pyochelin I methyl ester to those for 4-methylpyochelin I methyl ester, whose X-ray structure has been determined and relative stereochemistry assigned; (2) comparison of the rotation of the natural material to that of pyochelin I methyl ester synthesized from N-methyl-L-cysteine methyl ester, which is not expected to epimerize during the synthesis and thus assigns pyochelin I methyl ester as 4'R,2 '' R,4 '' R; and (3) the known facile epimerization at C-2 '' of 2 ''-substituted thiazolidine-4-carboxylic acids, which assigns the other (unfavored) naturally occurring isomer, pyochelin II, as 4'R,2 '' S,4 '' R. The remaining two synthetic products, neopyochelin I methyl ester and neopyochelin II methyl ester, were assigned the stereochemistry 4'S,2 '' S,4 '' R and 4'S,2 '' R,4 '' R, respectively, based on (1) the use of N-methyl-L-cysteine methyl ester in their synthesis, which establishes C-4 '' as R; (2) the known instability at C-2 '', which favors neopyochelin II (2 '' R) over neopyochelin I (2 '' S); and (3) the requirement of nonidentity with pyochelins I and II, which requires the S configuration at C-4'.