spiro 5'-(p-tolyl)-2',3'-dihydro-[1',3',4']thiadiazol-2',3-1,3-dihydro-5-methyl-indol-2-one

• 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: spiro 5'-(p-tolyl)-2',3'-dihydro-[1',3',4']thiadiazol-2',3-1,3-dihydro-5-methyl-indol-2-one
• 英文别名: 5-methyl-5'-(4-methylphenyl)-3'H-spiro[indole-3,2'-[1,3,4]thiadiazol]-2(1H)-one；5-methyl-5'-(4-methylphenyl)-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one；Thiadiazole derivative, 14；5-methyl-5'-(4-methylphenyl)spiro[1H-indole-3,2'-3H-1,3,4-thiadiazole]-2-one
• 化学式: C₁₇H₁₅N₃OS
• 分子量: 309.392
• InChiKey: JNGJBWPHVXFTBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲基靛红 、 4-Methyl-thiobenzoesaeure-hydrazid 以 乙醇 为溶剂， 生成 spiro 5'-(p-tolyl)-2',3'-dihydro-[1',3',4']thiadiazol-2',3-1,3-dihydro-5-methyl-indol-2-one
  参考文献：
  名称：

  5′-Phenyl-3′H-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2)

  摘要：

  5'-Phenyl-3' H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2) have been prepared via commercially available starting materials. Selected compounds 23, 33-35 show sub-micromolar ADAMTS-5 potency and strong SAR trends with selectivity over the related metalloproteases ADAMTS-4 (Aggrecanase-1), MMP12, and MMP13. This series of compounds represents progress toward a selective ADAMTS-5 inhibitor as a disease modifying osteoarthritis drug. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.048

文献信息

• Thiadiazole compounds and methods of use thereof
  申请人：Bursavich Matthew G.

  公开号：US20080125469A1

  公开（公告）日：2008-05-29

  The present invention relates to Thiadiazole Compounds; compositions comprising an effective dose of a Thiadiazole Compound; and methods treating or preventing a metalloproteinase-related disorder, such as, an arthritic disorder, osteoarthritis, cancer, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, atherosclerosis, age-related macular degeneration, myocardial infarction, a corneal ulceration, an ocular surface disease, hepatitis, an aortic aneurysm, tendonitis, a central nervous system disorder, abnormal wound healing, angiogenesis, restenosis, cirrhosis, multiple sclerosis, glomerulonephritis, graft versus host disease, diabetes, an inflammatory bowel disease, shock, invertebral disc degeneration, stroke, osteopenia or a periodontal disease or comprising administering an effective dose of a Thiadiazole Compound to a mammal in need thereof.

  本发明涉及噻二唑化合物；包含有效剂量噻二唑化合物的组合物；以及治疗或预防金属蛋白酶相关疾病的方法，例如关节炎、骨关节炎、癌症、类风湿性关节炎、哮喘、慢性阻塞性肺病、动脉粥样硬化、老年性黄斑变性、心肌梗死、角膜溃疡、眼表疾病、肝炎、主动脉瘤、肌腱炎、中枢神经系统疾病、异常伤口愈合、血管生成、再狭窄、肝硬化、多发性硬化、肾小球肾炎、移植物抗宿主病、糖尿病、炎症性肠病、休克、椎间盘退行性变、中风、骨质疏松症或牙周疾病，或包括向需要的哺乳动物施用有效剂量噻二唑化合物。
• THIADIAZOLE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Wyeth

  公开号：EP2032584A2

  公开（公告）日：2009-03-11
• [EN] THIADIAZOLE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE THIADIAZOLE ET PROCÉDÉS LES UTILISANT
  申请人：WYETH CORP

  公开号：WO2007146138A2

  公开（公告）日：2007-12-21

  [EN] The present invention relates to Thiadiazole Compounds; compositions comprising an effective dose of a Thiadiazole Compound; and methods treating or preventing a metalloproteinase-related disorder, such as, an arthritic disorder, osteoarthritis, cancer, rheumatoid arthritis, asthma, chronic obstructive pulmonary disease, atherosclerosis, age- related macular degeneration, myocardial infarction, a corneal ulceration, an ocular surface disease, hepatitis, an aortic aneurysm, tendonitis, a central nervous system disorder, abnormal wound healing, angiogenesis, restenosis, cirrhosis, multiple sclerosis, glomerulonephritis, graft versus host disease, diabetes, an inflammatory bowel disease, shock, invertebral disc degeneration, stroke, osteopenia or a periodontal disease or comprising administering an effective dose of a Thiadiazole Compound to a mammal in need thereof.
  [FR] La présente invention concerne des composés de thiadiazole ; des compositions comprenant une dose efficace d'un composé de thiadiazole ; et des procédés de traitement ou de prévention d'un trouble lié aux métalloprotéinases tel qu'un trouble arthritique, l'ostéoarthrite, le cancer, la polyarthrite rhumatoïde, l'asthme, la maladie pulmonaire obstructive chronique, l'athérosclérose, la dégénérescence maculaire liée à l'âge, l'infarctus du myocarde, une ulcération cornéenne, une maladie de la surface de l'oel, l'hépatite, un anévrisme aortique, la tendinite, un trouble du système nerveux central, la cicatrisation anormale, l'angiogenèse, la resténose, la cirrhose, la sclérose en plaques, la glomérulonéphrite, la maladie homologue, le diabète, une maladie entérique inflammatoire, le choc, la dégénérescence des disques intervertébraux, l'accident vasculaire cérébral, l'ostéopénie ou une maladie parodontique, comprenant l'administration d'une dose efficace d'un composé de thiadiazole à un mammifère nécessitant un tel traitement.