4-[(4-氟苯基)甲氧基]苯磺酰氯 | 210755-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(4-氟苯基)甲氧基]苯磺酰氯
• 英文名称: 4-(4-fluorobenzyloxy)benzene-1-sulfonyl chloride
• 英文别名: 4-(4-Fluoro-benzyloxy)-benzenesulfonyl chloride；4-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride；4-[(4-fluorophenyl)methoxy]benzenesulfonyl chloride
• CAS: 210755-57-0
• 化学式: C₁₃H₁₀ClFO₃S
• mdl: MFCD09813241
• 分子量: 300.738
• InChiKey: DAABFHOAKKNNRE-UHFFFAOYSA-N

物化性质

• 沸点：
  431.1±25.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(4-氟苯基)甲氧基]苯磺酰氯 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-(4-(4-fluorobenzyloxy)phenylsulfonamido)-N-hydroxyacetamide
  参考文献：
  名称：

  Selective Arylsulfonamide Inhibitors of ADAM-17: Hit Optimization and Activity in Ovarian Cancer Cell Models

  摘要：

  Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nivi on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.

  DOI：

  10.1021/jm4011753
• 作为产物：
  描述：

  sodium p-hydroxybenzenesulfonate 在 草酰氯 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 48.0h， 生成 4-[(4-氟苯基)甲氧基]苯磺酰氯
  参考文献：
  名称：

  Selective Arylsulfonamide Inhibitors of ADAM-17: Hit Optimization and Activity in Ovarian Cancer Cell Models

  摘要：

  Activated leukocyte cell adhesion molecule (ALCAM) is expressed at the surface of epithelial ovarian cancer (EOC) cells and is released in a soluble form (sALCAM) by ADAM-17-mediated shedding. This process is relevant to EOC cell motility and invasiveness, which is reduced by inhibitors of ADAM-17. In addition, ADAM-17 plays a key role in EGFR signaling and thus may represent a useful target in anticancer therapy. Herein we report our hit optimization effort to identify potent and selective ADAM-17 inhibitors, starting with previously identified inhibitor 1. A new series of secondary sulfonamido-based hydroxamates was designed and synthesized. The biological activity of the newly synthesized compounds was tested in vitro on isolated enzymes and human EOC cell lines. The optimization process led to compound 21, which showed an IC50 of 1.9 nivi on ADAM-17 with greatly increased selectivity. This compound maintained good inhibitory properties on sALCAM shedding in several in vitro assays.

  DOI：

  10.1021/jm4011753
• 作为试剂：
  描述：

  sodium 4-(4-fluorobenzyloxy)benzenesulfonate 、 氯化亚砜 在 N,N-二甲基甲酰胺 4-[(4-氟苯基)甲氧基]苯磺酰氯 作用下， 反应 8.0h， 生成 4-[(4-氟苯基)甲氧基]苯磺酰氯
  参考文献：
  名称：

  Arylsulfonyl hydroxamic acid derivatives

  摘要：

  一种化合物，其化学式为上述定义的R1、R2、R3、R4、R5、R6、R7、R8、R9和Q，可用于治疗所选疾病，包括关节炎、癌症、组织溃疡、黄斑变性、再狭窄、牙周病、表皮松解症、巩膜炎和其他以基质金属蛋白酶活性为特征的疾病、艾滋病、败血症、脓毒症休克和其他涉及TNF产生的疾病。此外，本发明的化合物可与标准非甾体抗炎药（NSAID'S）和镇痛药一起联合治疗，并与细胞毒性药物（如阿霉素、多柔比星、顺铂、依托泊苷、紫杉醇、替-taxotere和其他生物碱，如长春碱）联合使用，用于癌症治疗。

  公开号：

  US06599890B1

文献信息

• (4-arylsulfonylamino)-tetrahydropyran-4-carboxylic acid hydroxamides
  申请人：Pfizer Inc.

  公开号：US06087392A1

  公开（公告）日：2000-07-11

  A compound of the formula ##STR1## wherein Q is as defined above, are useful in the treatment of a condition selected from the group consisting of arthritis (including osteoarthritis and rheumatoid arthritis), inflammatory bowel disease, Crohn's disease, emphysema, chronic obstructive pulmonary disease, Alzheimer's disease, organ transplant toxicity, cachexia, allergic reactions, allergic contact hypersensitivity, cancer, tissue ulceration, restenosis, periodontal disease, epidermolysis bullosa, osteoporosis, loosening of artificial joint implants, atherosclerosis (including atherosclerotic plaque rupture), aortic aneurysm (including abdominal aortic aneurysm and brain aortic aneurysm), congestive heart failure, myocardial infarction, stroke, cerebral ischemia, head trauma, spinal cord injury, neuro-degenerative disorders (acute and chronic), autoimmune disorders, Huntington's disease, Parkinson's disease, migraine, depression, peripheral neuropathy, pain, cerebral amyloid angiopathy, nootropic or cognition enhancement, amyotrophic lateral sclerosis, multiple sclerosis, ocular angiogenesis, corneal injury, macular degeneration, abnormal wound healing, burns, diabetes, tumor invasion, tumor growth, tumor metastasis, corneal scarring, scleritis, AIDS, sepsis and septic shock. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID'S) and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer.

  公式为##STR1##的化合物，在治疗以下疾病方面是有用的：关节炎（包括骨关节炎和类风湿关节炎）、炎症性肠病、克罗恩病、肺气肿、慢性阻塞性肺病、阿尔茨海默病、器官移植毒性、虚弱症、过敏反应、过敏性接触性过敏症、癌症、组织溃疡、再狭窄、牙周病、表皮溃疡性水疱病、骨质疏松症、人工关节植入物松动、动脉粥样硬化（包括动脉粥样硬化斑块破裂）、主动脉瘤（包括腹主动脉瘤和脑主动脉瘤）、充血性心力衰竭、心肌梗死、中风、脑缺血、头部创伤、脊髓损伤、神经退行性疾病（急性和慢性）、自身免疫性疾病、亨廷顿病、帕金森病、偏头痛、抑郁症、周围神经病、疼痛、脑淀粉样血管病、脑力增强剂或认知增强剂、肌萎缩侧索硬化、多发性硬化、眼部血管生成、角膜损伤、黄斑变性、异常伤口愈合、烧伤、糖尿病、肿瘤浸润、肿瘤生长、肿瘤转移、角膜瘢痕、巩膜炎、艾滋病、败血症和脓毒性休克。此外，本发明的化合物可与标准非甾体类抗炎药（NSAID'S）和镇痛药联合治疗，也可与阿霉素、多柔比星、顺铂、依托泊苷、紫杉醇、多西他赛和其他生物碱（如长春碱）等细胞毒药物联合治疗癌症。
• 3-(arylsulfonylamino)-tetrahydropyran-3-carboxylic acid hydroxamides
  申请人：Pfizer Inc

  公开号：US06197810B1

  公开（公告）日：2001-03-06

  A compound of the formula wherein R1, R2, R3, R4 and Q are as defined above, are useful in the treatment of arthritis (including osteoarthritis and rheumatoid arthritis), cancer and other diseases. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID's), COX-2 inhibitors and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer.

  其中R1、R2、R3、R4和Q如上定义，可用于治疗关节炎（包括骨关节炎和类风湿性关节炎）、癌症和其他疾病。此外，本发明的化合物可与标准非甾体抗炎药（NSAID's）、COX-2抑制剂和止痛药联合使用，也可与细胞毒性药物如阿霉素、道诺霉素、顺铂、依托泊苷、紫杉醇、多西他赛和其他生物碱如长春新碱联合用于治疗癌症。
• Hydroxy pipecolate hydroxamic acid derivatives
  申请人：Pfizer

  公开号：US06329397B1

  公开（公告）日：2001-12-11

  A compound of the formula wherein R1, R2 R3, R4 R5, R6, R7, R8, R9 and Ar are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, and other diseases characterized by matrix metalloproteinase or mammalian reprolysin activity. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID'S), COX-2 inhibitors and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer.

  其中R1、R2、R3、R4、R5、R6、R7、R8、R9和Ar如上定义，用于治疗由基质金属蛋白酶或哺乳动物再生酶活性引起的关节炎、癌症和其他疾病。此外，本发明的化合物可与标准非甾体抗炎药(NSAID'S)、COX-2抑制剂和镇痛药联合应用，也可与细胞毒药物如阿霉素、道诺霉素、顺铂、依托泊苷、紫杉醇、紫杉特尔和其他生物碱如长春新碱联合应用，用于治疗癌症。
• Arylsulfonylamino hydroxamic acid derivatives
  申请人：Pfizer Inc

  公开号：US06303636B1

  公开（公告）日：2001-10-16

  A compound of the formula wherein R1, R2 and Q are as defined above, useful in the treatment of a condition selected from the group consisting of arthritis, cancer, tissue ulceration, macular degeneration, restenosis, periodontal disease, epidermolysis bullosa, scleritis, and other diseases characterized by matrix metalloproteinase activity, AIDS, sepsis, septic shock and other diseases involving the production of TNF. In addition, the compounds of the present invention may be used in combination therapy with standard non-steroidal anti-inflammatory drugs (NSAID'S) and analgesics, and in combination with cytotoxic drugs such as adriamycin, daunomycin, cis-platinum, etoposide, taxol, taxotere and other alkaloids, such as vincristine, in the treatment of cancer,

  一种化合物的分子式，其中R1、R2和Q如上所定义，在治疗关节炎、癌症、组织溃疡、黄斑变性、再狭窄、牙周病、表皮溃疡性水疱病、巩膜炎以及其他以基质金属蛋白酶活性为特征的疾病，如艾滋病、败血症、感染性休克以及其他涉及TNF产生的疾病中有用。此外，本发明的化合物可与标准非甾体类抗炎药（NSAID'S）和镇痛药联合用于组合疗法，并可与阿霉素、多柔比星、顺铂、依托泊苷、紫杉醇、多西他赛以及其他生物碱（如长春碱）等细胞毒药物结合，用于癌症治疗。
• SUBSTITUTED TETRAHYDROISOQUINOLINES USED IN THE FORM OF MMP INHIBITORS, METHOD FOR THE PRODUCTION AND USE THEREOF IN THE FORM OF DRUGS
  申请人：Hofmeister Armin

  公开号：US20070203118A1

  公开（公告）日：2007-08-30

  The present invention is directed to a compound of formula (I) wherein R 1 , R 2 , R 3 , R 4 , A, L and n are as defined herein, or a pharmacologically acceptable salt thereof, its pharmaceutical composition and it use as a MMP inhibitor.

  本发明涉及一种具有以下化学式(I)的化合物，其中R1、R2、R3、R4、A、L和n如本文所定义，或其药理学上可接受的盐，以及其药物组合物及其作为MMP抑制剂的用途。