5-叔丁基-4-甲基-噻唑-2-胺 | 45865-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-叔丁基-4-甲基-噻唑-2-胺
• 英文名称: 5-(1,1-dimethyl)ethyl-4-methylthiazol-2-ylamine
• 英文别名: 2-amino-5-tert-butyl-4-methylthiazole；5-tert-butyl-4-methylthiazol-2-ylamine；5-t-Butyl-2-amino-4-methyl-thiazol；2-amino-5-t-butyl-4-methylthiazole；5-tert-butyl-4-methylthiazole-2-ylamine；5-tert-butyl-4-methylthiazol-2-amine；5-tert-Butyl-4-methyl-thiazol-2-ylamine；5-tert-butyl-4-methyl-1,3-thiazol-2-amine
• CAS: 45865-42-7
• 化学式: C₈H₁₄N₂S
• mdl: MFCD03724919
• 分子量: 170.279
• InChiKey: WCDNODZFXIBEJD-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  269.6±9.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934100090
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存放在室温、避光且处于惰性气体环境中的地方。

反应信息

• 作为反应物：
  描述：

  5-叔丁基-4-甲基-噻唑-2-胺 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 N-(5-tert-butyl-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene)-3-nitro-benzenesulfonamide
  参考文献：
  名称：

  Regioselective Alkylation of Thiazolylsulfonamides: Direct and Efficient Synthesis of 3‐Alkylthiazolidene Derivatives

  摘要：

  Various N-3-alkylated thiazolidenesulfonamide derivatives were efficiently prepared by the direct endo-selective alkylation of thiazolylsulfonamides. The effects of different bases and solvents were investigated, and the NaH-THF combination was found to be the most effective at conferring high yields and endo-selectivity.

  DOI：

  10.1080/00397910500186730
• 作为产物：
  描述：

  2-氨基-4-甲基噻唑 、 叔丁醇 在 硫酸 作用下， 生成 5-叔丁基-4-甲基-噻唑-2-胺
  参考文献：
  名称：

  氨基噻唑的烷基化

  摘要：

  DOI：

  10.1007/bf01031760

文献信息

• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  申请人：Florjancic S. Alan

  公开号：US20080058335A1

  公开（公告）日：2008-03-06

  The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1 , R 2 , R 3 , and L 1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1a , R 2a and (Rx)n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及式(I)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1 ，R 2 ，R 3 和L 1 在规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。本发明还涉及式(II)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1a ，R 2a 和(Rx)n如规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• Compounds Which Modulate The CB2 Receptor
  申请人：Berry Angela

  公开号：US20100009964A1

  公开（公告）日：2010-01-14

  Compounds of formula (I) are disclosed. Compounds according to the and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

  公式（I）的化合物已被披露。根据该公式的化合物对治疗炎症有用。那些是激动剂的化合物还额外适用于治疗疼痛。
• [EN] NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS EN TANT QUE LIGANDS DE RÉCEPTEUR DE CANNABINOÏDE ET LEURS UTILISATIONS
  申请人：ABBOTT LAB

  公开号：WO2009067613A1

  公开（公告）日：2009-05-28

  The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (I). wherein R1, R2, R3, R4, and L1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (II). wherein R1a, R2a, Rx, and n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及式(I)的化合物，或药用盐、前药、前药的盐或其组合物，式(I)。其中R1、R2、R3、R4和L1在规范中定义，包括含有这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。本发明还涉及式(II)的化合物，或药用盐、前药、前药的盐或其组合物，式(II)。其中R1a、R2a、Rx和n如规范中定义，包括含有这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。
• [EN] DIAZEPANE COMPOUNDS WHICH MODULATE THE CB2 RECEPTOR<br/>[FR] COMPOSÉS DE DIAZÉPANE QUI MODULENT LE RÉCEPTEUR CB2
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009055357A1

  公开（公告）日：2009-04-30

  Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

  公开了公式(I)的化合物。根据发明的化合物能够结合并成为CB2受体的激动剂、拮抗剂或反向激动剂，并且用于治疗炎症。其中作为激动剂的化合物还可额外用于治疗疼痛。
• Structure-Activity Relationships of 2-Aminothiazole Derivatives as Inducible Nitric Oxide Synthase Inhibitor
  作者：Shigeo Ueda、Hideo Terauchi、Motoji Kawasaki、Akihiro Yano、Motoharu Ido

  DOI：10.1248/cpb.52.634

  日期：——

  Nitric oxide synthase (NOS) has been divided into two major sub-enzymes, i.e. inducible NOS (iNOS) and constitutive NOS (cNOS). Although nitric oxide (NO) plays an important role as host defense mediator, excessive production of NO by iNOS has been involved in the pathology of many inflammatory diseases. Recently, we reported that the 2-imino-1,3-oxazolidine (1a) weakly inhibits iNOS and that introduction of an alkyl moiety on the oxazolidine ring of 1a enhances the inhibitory activity and selectivity for iNOS. In our search for better iNOS inhibitors, we focused our efforts on the 2-aminothiazole scaffold 3 as it possesses a ring similar to that of 1a. In this study, we evaluated the inhibitory activity of a series of 2-aminothiazole derivatives against both iNOS and neuronal NOS (nNOS). Our results show that introduction of appropriately-sized substituents at the 4- and 5-position of the 2-aminothiazole ring improves the inhibitory activity and selectivity for iNOS. We also found that the selectivity of 5a [5-(1-methyl)ethyl-4-methylthiazol-2-ylamine] and 5b [5-(1,1-dimethyl)ethyl-4-methylthiazol-2-ylamine] for iNOS was similar to that of oxazolidine derivative 1b (4-methyl-5-propyl-2-imino-1,3-oxazolidine) and much higher than that of L-NAME. However, we could not enhance the inhibitory activity against iNOS by introducing an alkyl substituent into the 2-aminothiazole ring as we could in the case of oxazolidine one. On the other hand, introduction of bulky or hydrophilic substituent at any position of the 2-aminothiazole ring remarkably decreased or even abolished the inhibitory activity against NOS.

  一氧化氮合酶（NOS）被分为两种主要的亚酶，即可诱导型一氧化氮合酶（iNOS）和构成型一氧化氮合酶（cNOS）。虽然一氧化氮（NO）在宿主防御中发挥重要作用，但iNOS过量产生NO已涉及许多炎症疾病的病理。最近，我们报告了2-亚氨基-1,3-噁唑烷（1a）对iNOS的抑制作用较弱，并且在1a的噁唑烷环上引入烷基基团可以增强对iNOS的抑制活性和选择性。在寻找更好的iNOS抑制剂时，我们将精力集中在2-氨基噻唑骨架3上，因为它具有类似于1a的环状结构。在本研究中，我们评估了一系列2-氨基噻唑衍生物对iNOS和神经型一氧化氮合酶（nNOS）的抑制活性。结果表明，在2-氨基噻唑环的4位和5位引入适当大小的取代基能显著提高对iNOS的抑制活性和选择性。我们还发现，5a [5-(1-甲基)乙基-4-甲基噻唑-2-胺]和5b [5-(1,1-二甲基)乙基-4-甲基噻唑-2-胺]对iNOS的选择性与噁唑烷衍生物1b（4-甲基-5-丙基-2-亚氨基-1,3-噁唑烷）相似，并且远高于 -NAME。然而，我们未能通过在2-氨基噻唑环上引入烷基取代基来增强对iNOS的抑制活性，正如在噁唑烷的情况下所实现的那样。另一方面，在2-氨基噻唑环的任何位置引入笨重或亲水性取代基显著降低甚至完全消除了对NOS的抑制活性。