4-(2-苯并噻唑基)-1-哌嗪羧酸叔丁酯 | 684217-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 4-(2-苯并噻唑基)-1-哌嗪羧酸叔丁酯
• 英文名称: tert-butyl 4-(benzo[d]thiazol-2-yl)piperazine-1-carboxylate
• 英文别名: tert-butyl 4-(benzothiazol-2-yl)piperazine-1-carboxylate；Tert-butyl 4-(1,3-benzothiazol-2-yl)piperazine-1-carboxylate
• CAS: 684217-29-6
• 化学式: C₁₆H₂₁N₃O₂S
• mdl: MFCD09028510
• 分子量: 319.428
• InChiKey: KVDXCOOWUVQJDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-苯并噻唑基)-1-哌嗪羧酸叔丁酯 在 水 、 sodium carbonate 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 (4-benzothiazol-2-yl-piperazin-1-yl)-acetic acid
  参考文献：
  名称：

  Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

  摘要：

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.011
• 作为产物：
  描述：

  4-(2-Bromo-phenylthiocarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester 在 copper(l) iodide 1,10-菲罗啉 、 caesium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以93%的产率得到4-(2-苯并噻唑基)-1-哌嗪羧酸叔丁酯
  参考文献：
  名称：

  Copper- and palladium-catalyzed intramolecular C–S bond formation: a convenient synthesis of 2-aminobenzothiazoles

  摘要：

  通过芳基卤化物和硫脲官能团之间的交叉耦合作用，铜和钯催化分子内 CâS 键的形成，证明了 2-氨基苯并噻唑的合成，其中铜催化的方案总体上优于钯催化的方案，且更具成本效益；铜催化的反应还进一步扩展了近期探索铜盐在碳对原子键形成反应中替代钯的实用性的研究。此外，还展示了一种将硫脲的合成和环化反应结合在一起的单锅变体。

  DOI：

  10.1039/b311591g

文献信息

• NOVEL 3-(4(BENZYLOXY)PHENYL)HEX-4-INOIC ACID DERIVATIVE, METHOD OF PREPARING SAME AND PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING METABOLIC DISEASE INCLUDING SAME AS EFFECTIVE INGREDIENT
  申请人：HYUNDAI PHARM CO., LTD

  公开号：US20160024063A1

  公开（公告）日：2016-01-28

  The present invention relates to a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, a preparation method thereof, and a pharmaceutical composition comprising the same as an active ingredient for the prevention and treatment of metabolic disease. The novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention has excellent activities of activating GPR40 protein and promoting insulin secretion accordingly but has no toxicity when co-administered with other drugs. That is, the novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention can be co-administered with other drugs and can promote the activation of GPR40 protein significantly, so that the composition comprising the same as an active ingredient can be efficiently used as a pharmaceutical composition for the prevention and treatment of metabolic disease such as obesity, type I diabetes, type II diabetes, incompatible glucose tolerance, insulin resistance, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, and syndrome X, etc.

  本发明涉及一种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物，其制备方法以及包含该衍生物作为活性成分的药物组合物，用于预防和治疗代谢性疾病。本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，对于激活GPR40蛋白并相应地促进胰岛素分泌具有优良活性，且在与其他药物联合使用时没有毒性。也就是说，本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，可以与其他药物联合使用，并且能显著促进GPR40蛋白的激活，使得包含其作为活性成分的组合物能有效地用作预防和治疗诸如肥胖、I型糖尿病、II型糖尿病、糖耐量异常、胰岛素抵抗、高血糖、高脂血症、高甘油三酯血症、高胆固醇血症、血脂异常和X综合症等代谢性疾病的药物组合物。
• Ru/C: a simple heterogeneous catalyst for the amination of azoles under ligand free conditions
  作者：K. Harsha Vardhan Reddy、B. S. P. Anil Kumar、V. Prakash Reddy、R. Uday Kumar、Y. V. D. Nageswar

  DOI：10.1039/c4ra05447d

  日期：——

  A ligand free Ru/C-catalyzed amination of 2-halo azoles with a broad scope of aminating reagents has been developed. Utilizing this protocol a variety of 2-aminoazole derivatives were synthesized in moderate to good yields. The methodology is operationally simple and it provides potentially useful products by using an inexpensive recyclable catalytic system.

  使用无配体的Ru/C催化剂对2-卤代唑类化合物进行胺化反应，可以使用广泛的胺化试剂。利用这一方法合成了多种2-氨基唑类衍生物，产率在中等到良好之间。该方法操作简单，并且通过使用廉价可回收的催化体系提供了潜在有用的产物。
• Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by CH Zincation
  作者：Stacey L. McDonald、Charles E. Hendrick、Qiu Wang

  DOI：10.1002/anie.201311029

  日期：2014.4.25

  Direct amination of heteroarenes and arenes has been achieved in a one‐pot CH zincation/copper‐catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and aromatic amines including those previously inaccessible using CH amination methods. The mild reaction conditions and good functional‐group compatibility

  杂芳烃和芳烃的直接胺化已经在一锅C - H锌化/铜催化的亲电胺化过程中实现。这种胺化方法提供了一种高效、快速的方法来获得各种杂芳胺和芳香胺，包括以前使用 C - H 胺化方法无法获得的胺。温和的反应条件和良好的官能团相容性证明了其在合成重要且复杂的胺类方面的巨大潜力。
• Copper-Catalyzed Electrophilic Amination of Benzoxazoles via Magnesation
  作者：Sangback Lee、Yunmi Lee

  DOI：10.1002/ejoc.201900335

  日期：2019.5.26

  A mild and efficient method for the synthesis of 2‐aminobenzoxazoles through a Cu‐catalyzed electrophilic amination of benzoxazole derivatives with O‐benzoyl hydroxylamines by direct magnesation has been developed.

  已经开发了一种温和有效的方法，该方法通过直接氧化反应，通过邻苯二甲酰基衍生物与邻苯二甲酰基羟胺的铜催化亲电胺化反应合成2-氨基苯并恶唑。
• 2-取代氧基-5-甲砜基苯基哌嗪酰胺类似物及 其制备方法和用途
  申请人：上海翰森生物医药科技有限公司

  公开号：CN105712952B

  公开（公告）日：2021-03-26

  本发明公开了2‑取代氧基‑5‑甲砜基苯基哌嗪酰胺类似物及其制备方法和用途。具体地，本发明涉及一种具有式(I)化合物2‑取代氧基‑5‑甲砜基苯基哌嗪酰胺类似物及其制备方法和应用，其中式(I)化合物中的取代基如说明书所定义。该系列化合物具有抑制甘氨酸转运蛋白‑1(GlyT1)的活性，可以用来治疗中枢神经及精神领域的相关疾病，例如精神分裂症(包括阳性症状、阴性症状以及认知性症状)、老年痴呆症、帕金森氏症以及其他的相关精神类疾病，在预防与治疗中枢神经及精神疾病药物中的具有广泛应用，有望开发成新一代GlyT1抑制剂。