(S)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydrothiazole-4-carboxamide | 338461-20-4

• 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
• 英文名称: (S)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydrothiazole-4-carboxamide
• 英文别名: (4S)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydro-1,3-thiazole-4-carboxamide
• CAS: 338461-20-4
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: LNDAMQPSKUBGQY-SECBINFHSA-N

物化性质

• 沸点：
  415.1±55.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydrothiazole-4-carboxamide 在 咪唑 、 lithium aluminium tetrahydride 、 potassium acetate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 生成
  参考文献：
  名称：

  使用SmI2介导的Reformatsky反应和Zn2 +诱导的不对称噻唑烷形成的短立体选择性合成前环皮素。

  摘要：

  前皮芽孢杆菌素（1）可能是皮西芽孢素生物合成中的一种中间体，铁皮芽孢杆菌是铁团菌，可吸收丹波雷杆菌亚种（细菌）的亚铁。piscicida，鱼巴氏杆菌病的病原体。通过收敛方法从1- / d-半胱氨酸和2-羟基苄腈开始合成化合物1。关键步骤是高度非对映选择性的SmI2介导的Reformatsky反应和Zn2 +诱导的不对称噻唑烷的形成，然后进行内酰胺化。为1建立了绝对构型9R，10S，12R，13S，这证实了先前基于NOE和计算方法提出的相对立体化学。

  DOI：

  10.1021/ol502958u
• 作为产物：
  描述：

  邻羟基苯甲腈 在 potassium carbonate 、 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 甲醇 、 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-2-(2-hydroxyphenyl)-N-methoxy-N-methyl-4,5-dihydrothiazole-4-carboxamide
  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

• Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin
  作者：Akira Ino、Akira Murabayashi

  DOI：10.1016/s0040-4020(01)00012-6

  日期：2001.3

  Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable C-9 carbon was preserved during cyclization of β-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S

  完成了耶尔西菌素的全合成，这是一种来自小肠结肠炎耶尔森氏菌培养物的铁载体。在β-羟基硫酰胺的环化过程中，通过伯硫试剂生成噻唑啉，可以保持易于消旋的C-9碳的手性。根据它的合成，天然耶尔森杆菌的绝对构型已被确定为9 - [R，10个RS，12 - [R，13小号和19小号。
• Biologically Inspired Total Synthesis of Ulbactin F, an Iron-Binding Natural Product
  作者：Justin A. Shapiro、Kelly R. Morrison、Shreya S. Chodisetty、Djamaladdin G. Musaev、William M. Wuest

  DOI：10.1021/acs.orglett.8b02599

  日期：2018.9.21

  environmental microbiomes provide exquisite templates for elucidating biological activity in the search for new drugs. A recently discovered marine Brevibacillus sp. metabolite, ulbactin F, was found to inhibit tumor cell migration and invasion at IC50 < 3 μM. Herein, we disclose the first total synthesis of ulbactin F and epi-ulbactin F, which was modeled after the biosynthetic pathway. The scaffold bears

  来自环境微生物组的天然产物为阐明新药寻找中的生物活性提供了精美的模板。最近发现的一种海洋短芽孢杆菌。代谢物 ulbactin F 被发现可抑制肿瘤细胞迁移和侵袭，IC 50 < 3 μM。在此，我们公开了 ulbactin F 和epi -ulbactin F的首次全合成，这是根据生物合成途径建模的。该支架与人类病原体的铁载体结构相似，但包含源自半胱氨酸的新型三环系统。我们发现ulbactin F形成低亲和力金属配合物，优先选择Fe 3+和Cu 2+，这可能暗示了其环境作用及其抗转移作用机制。
• Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold
  作者：Sabrina Noël、Laurent Guillon、Isabelle J. Schalk、Gaëtan L. A. Mislin

  DOI：10.1021/ol1028173

  日期：2011.3.4

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.
• [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING INFLAMMATORY BOWEL DISEASE<br/>[FR] COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES DE TRAITEMENT D'UNE MALADIE INTESTINALE INFLAMMATOIRE
  申请人：[en]FLAGSHIP PIONEERING INNOVATIONS VI, LLC

  公开号：WO2023192388A1

  公开（公告）日：2023-10-05

  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.