2-(2-Hydroxyphenyl)thiazole-4-carboxaldehyde | 118446-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-Hydroxyphenyl)thiazole-4-carboxaldehyde
• 英文别名: 2-(2-Hydroxyphenyl)-2-thiazoline-4-carboxaldehyde；2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carbaldehyde；4,5-Dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxaldehyde；2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carbaldehyde
• CAS: 118446-23-4
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: NINIAHXJBYQIFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.9±52.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 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：
  75
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Hydroxyphenyl)thiazole-4-carboxaldehyde 在 potassium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 28.0h， 生成 (4S)-2-(2-(2-hydroxyphenyl)-4,5-dihydrothiazol-4-yl)-3,4-dimethylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING INFLAMMATORY BOWEL DISEASE
  [FR] COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES DE TRAITEMENT D'UNE MALADIE INTESTINALE INFLAMMATOIRE

  摘要：

  The disclosure provides pharmaceutical compositions comprising a therapeutically effective amount of compound (A), compound (B), compound (C), compound (D), compound (E), compound (F), compound (G), compound (H), compound (J), compound (K), compound (L), compound (M), compound (N), compound (O), compound (P), or compound (Q)or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient: Also provided are dosage units comprising one or more of compound (A), compound (B), compound (C), compound (D), compound (E), compound (F), compound (G), compound (H), compound (J), compound (K), compound (L), compound (M), compound (N), compound (O), compound (P), or compound (Q) or the pharmaceutical compositions described herein, methods of treating an inflammatory bowel disease in a subject in need thereof, or methods of modulating an inflammatory bowel disease marker in a subject in need thereof.

  公开号：

  WO2023192388A1
• 作为产物：
  描述：

  (S)-2-(2-hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid 在 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 2-(2-Hydroxyphenyl)thiazole-4-carboxaldehyde
  参考文献：
  名称：

  聚合的古铁青霉素为Ga 3+配合物的全合成

  摘要：

  含铁细胞piscibactin是参与致病细菌的铁摄取的主要毒力因子发光菌damselae亚种。piscicida和Anguillarum弧菌分别负责鱼类细菌光致细菌（巴氏杆菌病）和弧菌病。描述了使用l- / d-半胱氨酸作为手性试剂和梅德鲁姆酸的Ga 3+络合物的收敛全合成。酸敏感的β-羟基-2,4-二取代的噻唑啉部分和方便的保护基团的合成中的Staudinger还原/ Aza-Wittig工艺是该合成的关键步骤。

  DOI：

  10.1021/acs.orglett.0c03850

文献信息

• Watasemycin biosynthesis in Streptomyces venezuelae: thiazoline C-methylation by a type B radical-SAM methylase homologue
  作者：Yuki Inahashi、Shanshan Zhou、Maureen J. Bibb、Lijiang Song、Mahmoud M. Al-Bassam、Mervyn J. Bibb、Gregory L. Challis

  DOI：10.1039/c6sc03533g

  日期：——

  A type B radical-SAM methylase homologue catalyses thiazoline C-methylation as the final step of watasemycin biosynthesis in Streptomyces venezuelae ATCC10712.

  一种B型基团-SAM甲基转移酶同源物在Streptomyces venezuelae ATCC10712中催化噻唑环C-甲基化作为watasemycin生物合成的最后一步。
• Structural Requirements for Ga³⁺ Coordination in Synthetic Analogues of the Siderophore Piscibactin Deduced by Chemical Synthesis and Density Functional Theory Calculations
  作者：M. Carmen de la Fuente、Lucía Ageitos、Marta A. Lages、Diana Martínez-Matamoros、Abel M. Forero、Miguel Balado、Manuel L. Lemos、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/acs.inorgchem.3c00787

  日期：2023.5.15

  α-methylthiazoline moiety does not affect such coordination. A complete 1H and 13C NMR chemical shift assignment of the diastereoisomer mixtures around C9/C10 was done for diagnostic stereochemical disposition. Additionally, density functional theory calculations were performed not only for confirming the stereochemistry of the Ga3+ complex among the six possible diastereoisomers but also for deducing the ability of

  进行了几种 piscibactin (Pcb) 类似物的立体选择性全合成，该类似物是由不同致病性革兰氏阴性菌产生的铁载体。酸敏感的 α -甲基噻唑啉部分被更稳定的噻唑环取代，不同之处在于 C-13 位置的 OH 基团的构型。这些 Pcb 类似物作为 Fe 3+的模拟物与 Ga 3+形成络合物的能力表明，C-13 处的羟基作为 13 S的构型对于 Ga 3+的螯合以保持金属配位至关重要，而噻唑环而不是α-甲基噻唑啉部分的存在不影响这种配位。一个完整的1C9/C10 附近的非对映异构体混合物的1H 和13 C NMR 化学位移分配用于诊断立体化学处置。此外，密度泛函理论计算不仅用于确认六种可能的非对映异构体中Ga 3+络合物的立体化学，还用于推断它们与镓形成八面体配位球的能力。最后，Pcb 和 Pcb 噻唑类似物 Ga 3+配合物对鳗弧菌缺乏抗菌活性同意铁载体在保护病原体免受金属离子毒性中的作
• 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'.