5-pentyl-thiazol-2-ylamine | 383131-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-pentyl-thiazol-2-ylamine
• 英文别名: 5-Pentyl-thiazol-2-ylamin；2-Amino-5-pentylthiazole；5-pentyl-1,3-thiazol-2-amine
• CAS: 383131-93-9
• 化学式: C₈H₁₄N₂S
• 分子量: 170.279
• InChiKey: AYNGEGJQFSDMCG-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  286.0±9.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-pentyl-thiazol-2-ylamine 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 2-Pentyl-6-phenylimidazo[2,1-b][1,3]thiazole
  参考文献：
  名称：

  6-Thienyl and 6-phenylimidazo[2,1-b]thiazoles as inhibitors of mitochondrial NADH dehydrogenase

  摘要：

  Starting from the potent inhibitory effect of the previously described 2 methyl-6-(2-thienyl)imidazo[2,1-b]thiazol on mitochondrial complex I, we prepared a series of derivatives in order to study the effect of a different substitution at the positions 2, 5 and 6. The replacement of the thienyl group at position 6 with a phenyl group does not modify the biological behaviour of the lead compound, whereas the shift of the methyl group from position 2 to position 5 yields a compound devoid of inhibitory effects. In both the 6-thienyl and 6-phenyl series, the lengthening of the chain at position 2 has provided useful information to outline the structural determinants of the ubiquinone antagonist action in imidazothiazole derivatives. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00203-2
• 作为产物：
  描述：

  庚醛 在 5,5-二溴巴比妥酸 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 5-pentyl-thiazol-2-ylamine
  参考文献：
  名称：

  Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer’s disease

  摘要：

  High-throughput screening with cyclin-dependent kinase 5 (cdk5)/p25 led to the discovery of N-(5-isopropyl-thiazol-2-yl)isobutyramide (1). This compound is an equipotent inhibitor of cdk5 and cyclin-dependent kinase 2 (cdk2)/cyclin E (IC50 = ca. 320nM). Parallel and directed synthesis techniques were utilized to explore the SAR of this series. Up to 60-fold improvements in potency at cdk5 and 12-fold selectivity over cdk2 were achieved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.006

文献信息

• [EN] 5-ARYL-THIAZOL-2-YL-AMINE COMPOUNDS AND THEIR THERAPEUTIC USE<br/>[FR] COMPOSÉS 5-ARYL-THIAZOL -2-YL-AMINE ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：CHARLES MARK DAVID

  公开号：WO2015025172A1

  公开（公告）日：2015-02-26

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to certain 5-aryl-thiazol-2-yl-amine compounds of the following formula (I) (for convenience, collectively referred to herein as "5AT2A compounds"), which, inter alia, inhibit LIM kinase (LIMK) activity. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit LIMK activity, and in the treatment of diseases and conditions that are mediated by LIMK, that are ameliorated by the inhibition of LIMK activity, etc., including proliferative conditions such as cancer (e.g., breast cancer, prostate cancer, melanoma, glioma, etc.), as well as vasodilation (including, e.g., hypertension, angina, cerebral vasospasm, and ischemia following subarachnoid hemorrhage), neurodegenerative disorders, atherosclerosis, fibrosis, and inflammatory diseases (including, e.g., Crohn's disease and chronic obstructive pulmonary disease (COPD)), and glaucoma (also known as ocular hypertension). (Formula (I))

  本发明一般涉及治疗化合物领域，更具体地涉及以下式(I)的某些5-芳基噻唑-2-基胺化合物（为方便起见，以下统称为“5AT2A化合物”），其中，这些化合物等抑制LIM激酶（LIMK）活性。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物和组合物，无论是体外还是体内，来抑制LIMK活性，并在治疗由LIMK介导的疾病和症状中发挥作用，这些疾病和症状通过抑制LIMK活性得到改善，等等，包括增生性疾病，如癌症（例如乳腺癌、前列腺癌、黑色素瘤、胶质瘤等），以及血管舒张（包括高血压、心绞痛、脑血管痉挛以及蛛网膜下腔出血后的缺血），神经退行性疾病、动脉粥样硬化、纤维化和炎症性疾病（包括克罗恩病和慢性阻塞性肺病（COPD）等），以及青光眼（也称为眼压增高）。
• Zur Synthese von 2-Amino-thiazolderivaten
  作者：H. Erlenmeyer、L. Herzfeld、B. Prijs

  DOI：10.1002/hlca.19550380529

  日期：——

  2-Aminothiazole and its 5-substituted derivatives were obtained in one step from thiourea and an aldehyde by reaction with sulfuryl chloride, bromine, iodine or nitric acid.

  通过与硫酰氯，溴，碘或硝酸反应，从硫脲和醛一步获得2-氨基噻唑及其5-取代的衍生物。
• Antiallergic and antiulcer
  申请人：Pfizer Inc.

  公开号：US04423048A1

  公开（公告）日：1983-12-27

  Antiallergy and antiulcer agents having the formula (I), ##STR1## and their pharmaceutically acceptable salts, wherein R.sub.1 and R.sub.2 taken separately are each hydrogen or lower alkyl; and R.sub.1 and R.sub.2 taken together are alkylene of 3-9 carbon atoms or phenylalkylene of 9-11 carbon atoms, with the proviso that the ring so formed is between 5- and 8-membered; acids of the formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.3 is hydrogen, which are useful as intermediates for compounds of the formula (I), but in many instances also possess the same useful biological activity as do formula I compounds; and intermediates of the formula II wherein R.sub.1 and R.sub.2 are defined as above, and R.sub.3 is alkyl of 1 to 4 carbon atoms, carbalkoxy of 2 to 5 carbon atoms, carbophenoxy or carbobenzoxy, are also described.

  具有以下公式（I）的抗过敏和抗溃疡剂及其药学上可接受的盐，其中R.sub.1和R.sub.2分别为氢或低碳基；而R.sub.1和R.sub.2在一起则为3-9个碳原子的烷基或9-11个碳原子的苯基烷基，但所形成的环在5-8个成员之间；具有以下公式（II）的酸，其中R.sub.1和R.sub.2如上所定义，而R.sub.3为氢，这些酸对于公式（I）化合物的中间体是有用的，但在许多情况下，它们也具有与公式I化合物相同的有用生物活性；还描述了公式II的中间体，其中R.sub.1和R.sub.2如上所定义，而R.sub.3为1-4个碳原子的烷基，2-5个碳原子的羧基烷基，羧基苯氧基或羧基苯甲氧基。
• 1-Oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides
  申请人：Pfizer Inc.

  公开号：US04414388A1

  公开（公告）日：1983-11-08

  Antiallergy and antiulcer agents having the formula (I), ##STR1## and their pharmaceutically acceptable salts, wherein R.sub.1 and R.sub.2 taken separately are each hydrogen or lower alkyl; and R.sub.1 and R.sub.2 taken together are alkylene of 3-9 carbon atoms or phenylalkylene of 9-11 carbon atoms, with the proviso that the ring so formed is between 5- and 8-membered; acids of the formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are as defined above and R.sub.3 is hydrogen, which are useful as intermediates for compounds of the formula (I), but in many instances also possess the same useful biological activity as do formula I compounds; and intermediates of the formula II wherein R.sub.1 and R.sub.2 are defined as above, and R.sub.3 is alkyl of 1 to 4 carbon atoms, carbalkoxy of 2 to 5 carbon atoms, carbophenoxy or carbobenzoxy, are also described.

  具有以下式子（I）的抗过敏和抗溃疡剂，以及它们的药学上可接受的盐：##STR1## 其中R.sub.1和R.sub.2分别为氢或低碳基；而R.sub.1和R.sub.2在一起则为3-9个碳原子的烷基或9-11个碳原子的苯基烷基，但所形成的环在5-8个成员之间；式子（II）的酸：##STR2## 其中R.sub.1和R.sub.2如上所定义，而R.sub.3为氢，这些酸是化合物（I）的中间体，但在许多情况下也具有与化合物（I）相同的有用生物活性；还描述了式子II的中间体，其中R.sub.1和R.sub.2如上所定义，而R.sub.3为1-4个碳原子的烷基，2-5个碳原子的羰基烷氧基，羰基苯氧基或羰基苯甲氧基。
• Prodrugs of substituted polycyclic compounds useful for selective inhibition of the coagulation cascade
  申请人：Pharmacia Corporation

  公开号：US20040082585A1

  公开（公告）日：2004-04-29

  The present invention relates to prodrug compounds, compositions and methods useful for preventing and treating thrombotic conditions in mammals. The prodrug compounds of the present invention selectively inhibit certain proteases of the coagulation cascade.

  本发明涉及一种用于预防和治疗哺乳动物血栓性疾病的前药化合物、组合物和方法。本发明的前药化合物选择性地抑制凝血级联反应中的某些蛋白酶。