tert-butyl methyl(6-methylpyridin-2-yl)carbamate | 205676-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl methyl(6-methylpyridin-2-yl)carbamate
• 英文别名: tert-butyl N-methyl-N-(6-methylpyridin-2-yl)carbamate
• CAS: 205676-84-2
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: UZRQBXOOMIFFLB-UHFFFAOYSA-N

物化性质

• 沸点：
  313.2±30.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  tert-butyl methyl(6-methylpyridin-2-yl)carbamate 在 lithium aluminium tetrahydride 、 硫酸 、 四丁基氟化铵 、 三苯基膦 、 三氟乙酸 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 ethyl 3-(6-{2-[6-(methylamino)-2-pyridyl]ethoxy}benzo[b]furan-3-yl)propanoate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Novel Potent and Selective α_vβ₃/α_vβ₅ Integrin Dual Inhibitors with Improved Bioavailability. Selection of the Molecular Core

  摘要：

  A novel series of potent and selective alpha(v)beta(3)/alpha(v)beta(5) dual inhibitors was designed, synthesized, and evaluated against several integrins. These compounds were synthesized through a Mitsunobu reaction between the guanidinium mimetics and the corresponding central templates. Guanidinium mimetics with enhaced rigidity (i.e., (2-pyridylamino)propoxy versus the 2-(6-methylamino-2-pyridyl)ethoxy) led to improved activity toward alpha(v)beta(3). Exemplary oral bioavailability in mice was achieved using the indole central scaffold. Although, oral bioavailability was maintained when the indole molecular core was replace with the bioisosteric benzofuran or benzothiophene ring systems, it was found to not significantly impact the integrin activity or selectivity. However, the indole series displayed the best in vivo pharmacokinetic properties. Thus, the indole series was selected for further structure-activity relationships to obtain more potent alpha(v)beta(3)/alpha(v)beta(5) dual antagonist with improved oral bioavailability.

  DOI：

  10.1021/jm049725u
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 tert-butyl methyl(6-methylpyridin-2-yl)carbamate
  参考文献：
  名称：

  2,6-Diaminopyridine Compounds Suitable For Treating Diseases Associated With Amyloid Or Amyloid-Like Proteins Or For Treating Or Preventing Ocular Diseases Or Conditions Associated With A Pathological Abnormality/Change In The Tissue Of The Visual System

  摘要：

  本发明涉及2,6-二氨基吡啶化合物，可用于治疗与淀粉样蛋白相关的一组疾病和异常以及与淀粉样蛋白类似蛋白相关的疾病或病况。本发明的化合物还可用于治疗与视觉系统组织中的病理异常/变化相关的眼部疾病。

  公开号：

  US20110092537A1

文献信息

• Substituted indoles and their use as integrin antagonists
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20020169200A1

  公开（公告）日：2002-11-14

  The present invention relates to novel substituted indole compounds that are antagonists of alpha V (&agr;v) integrins, for example &agr; v &bgr; 3 and &agr; v &bgr; 5 integrins, their pharmaceutically acceptable salts, and pharmaceutical compositions thereof. The compounds may be used in the treatment of pathological conditions mediated by &agr; v &bgr; 3 and &agr; v &bgr; 5 integrins, including such conditions as tumor growth, metastasis, restenosis, osteoporosis, inflammation, macular degeneration, diabetic retinopathy, and rheumatoid arthritis. The compounds have the general formula: 1 where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , D, X, W, a, m, n, i, j, k and v are defined herein.

  本发明涉及新型取代吲哚化合物，其为αV（αv）整合素的拮抗剂，例如αvβ3和αvβ5整合素，其药学上可接受的盐以及其药物组合物。这些化合物可用于治疗由αvβ3和αvβ5整合素介导的病理性状况，包括肿瘤生长、转移、再狭窄、骨质疏松、炎症、黄斑变性、糖尿病视网膜病变和类风湿性关节炎等病症。这些化合物具有以下一般式： 1 其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、D、X、W、a、m、n、i、j、k和v在此处定义。
• Method for stimulating bone formation
  申请人：SmithKline Beecham Corporation

  公开号：US20020032187A1

  公开（公告）日：2002-03-14

  A method for stimulating bone formation by administering integrin binding compounds which cause the release of osteocalcin from osteoblasts is disclosed.

  通过给予能够引发骨细胞释放骨钙蛋白的整合素结合化合物来刺激骨形成的方法被揭示。
• Facile preparation of thiophene C2-ethers using the Mitsunobu reaction
  作者：Craig S. Harris、Hervé Germain、Georges Pasquet

  DOI：10.1016/j.tetlet.2008.07.153

  日期：2008.10

  The preparation of thiophene ethers generally requires forcing conditions thus limiting the choice of alkyl substituent. Herein, we report the first successful generally applicable conditions for the selective O-alkylation of 2(5H)-thiophenone.

  噻吩醚的制备通常需要强制条件，因此限制了烷基取代基的选择。在这里，我们报道了2（5 H）-噻吩的选择性O-烷基化的第一个成功的普遍适用条件。
• Vitronectin receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US20030125317A1

  公开（公告）日：2003-07-03

  Compounds having a benzodiazepinyl core structure are disclosed which are vitronectin receptor antagonists useful in the treatment of osteoporosis, angiogenesis, tumor growth and metastasis, atherosclerosis, restenosis and inflammation.

  本文披露了具有苯二氮卓环核结构的化合物，这些化合物是维腾蛋白受体拮抗剂，可用于治疗骨质疏松症、血管生成、肿瘤生长和转移、动脉粥样硬化、再狭窄和炎症。
• Synthesis and structure–activity relationship of 2,6-disubstituted pyridine derivatives as inhibitors of β-amyloid-42 aggregation
  作者：Heiko Kroth、Nampally Sreenivasachary、Anne Hamel、Pascal Benderitter、Yvan Varisco、Valérie Giriens、Paolo Paganetti、Wolfgang Froestl、Andrea Pfeifer、Andreas Muhs

  DOI：10.1016/j.bmcl.2016.05.040

  日期：2016.7

  disease. Novel 2,6-disubstituted pyridine derivatives were designed to interact with the β-sheet conformation of Aβ via donor–acceptor–donor hydrogen bond formation. A series of pyridine derivatives were synthesized and tested regarding their potential to inhibit the aggregation of Aβ. The 2,6-diaminopyridine moiety was identified as a key component to inhibit Aβ aggregation. Overall, compounds having

  据推测，淀粉样β蛋白聚集是阿尔茨海默氏病发病机理中的关键事件。新型2，6-二取代吡啶衍生物经设计可通过供体-受体-供体氢键形成与Aβ的β-折叠构象相互作用。合成了一系列吡啶衍生物，并对其抑制Aβ聚集的潜力进行了测试。2，6-二氨基吡啶部分被鉴定为抑制Aβ聚集的关键成分。总体而言，具有被至少一个C 2-或C 3-接头隔开的三个3，2，6-二取代的吡啶单元的化合物表现出对Aβ聚集的最有效抑制。