1-(tert-butoxycarbonyl)-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine | 259807-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(tert-butoxycarbonyl)-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine
• 英文别名: 1-tert-butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine；tert-butyl 4-[1-(benzenesulfonyl)-5-chloroindol-2-yl]sulfonylpiperazine-1-carboxylate
• CAS: 259807-33-5
• 化学式: C₂₃H₂₆ClN₃O₆S₂
• 分子量: 540.061
• InChiKey: IKVUABKMKKZJJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.05h， 生成 1-(5-chloroindol-2-ylsulfonyl)4-[4-(pyridin-4-yl)benzoyl]piperazine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006
• 作为产物：
  描述：

  1-(苯磺酰基)-5-氯吲哚 在 叔丁基锂 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 11.0h， 生成 1-(tert-butoxycarbonyl)-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine
  参考文献：
  名称：

  Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites

  摘要：

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.006

文献信息

• NOVEL SULFONYL DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1104754A1

  公开（公告）日：2001-06-06

  Sulfonyl derivatives represented by the following general formula (I): Q1-Q2-T1-Q3-SO2-QA and drugs containing the same (wherein Q1 is an optionally substituted, saturated or unsaturated, five- or six-membered cyclic hydrocarbon group, a five- or six-membered heterocyclic group, or the like; Q2 is a single band, oxygen, sulfur, C1-C6 alkylene or the like; QA is optionally substituted arylalkenyl, heteroarylalkenyl or the like; and T1 is carbonyl or the like). These compounds have potent FXa-inhibitory effects and promptly exert satisfactory and persistent antithrombotic effects through oral administration, thus being useful as anticoagulant agents little accompanied with side effects.

  以下是通用公式（I）所代表的磺酰衍生物：Q1-Q2-T1-Q3-SO2-QA以及含有这些衍生物的药物（其中Q1是可选择地取代的饱和或不饱和的五元或六元环烃基团，五元或六元杂环基团等；Q2是单键，氧，硫，C1-C6烷基或类似物；QA是可选择地取代的芳基烯烃基团，杂环芳基烯烃基团或类似物；T1是羰基或类似物）。这些化合物具有强大的FXa抑制作用，并通过口服迅速产生令人满意且持久的抗血栓作用，因此可作为几乎不伴随副作用的抗凝血剂。
• Novel sulfonyl derivatives
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：US20040082611A1

  公开（公告）日：2004-04-29

  Described in the present invention are a sulfonyl derivative represented by the following formula (I): Q 1 -Q 2 -T 1 -Q 3 -SO 2 -Q A (I) [wherein Q 1 represents a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group, 5- or 6-membered heterocyclic group, dicyclic fused ring or tricyclic fused ring group which may have a substituent; Q 2 represents a single bond, an oxygen atom, a sulfur atom, a linear or branched C 1-6 alkylene group or the like; Q A represents an arylalkenyl group which may have a substituent or a heteroarylalkenyl group which may have a substituent; and T 1 represents a carbonyl group or the like] and a medicament comprising the same. The compound has strong FXa inhibitory action, provides prompt, sufficient and long-lasting anti-thrombus effects when orally administered, and has low side effects and is therefore useful as an excellent anticoagulant.

  本发明描述了一种由以下式(I)表示的磺酰基衍生物： Q1-Q2-T1-Q3-SO2-QA(I) [其中，Q1表示饱和或不饱和的5-或6-环烃基、5-或6-杂环基、二环融合环或三环融合环基，可能具有取代基；Q2表示单键、氧原子、硫原子、线性或支链的C1-6烷基等；QA表示可能具有取代基的芳基烯基或杂芳基烯基；T1表示羰基基团或类似物]，以及包含该化合物的药物。该化合物具有强烈的FXa抑制作用，口服后提供快速、充分和持久的抗血栓效果，并且具有低副作用，因此可用作优秀的抗凝剂。
• Sulfonyl derivatives
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US06747023B1

  公开（公告）日：2004-06-08

  Described in the present invention are a sulfonyl derivative represented by the following formula (I): Q1—Q2—T1—Q3—SO2—QA  (I) [wherein Q1 represents a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group, 5- or 6-membered heterocyclic group, dicyclic fused ring or tricyclic fused ring group which may have a substituent; Q2 represents a single bond, an oxygen atom, a sulfur atom, a linear or branched C1-6 alkylene group or the like; QA represents an arylalkenyl group which may have a substituent or a heteroarylalkenyl group which may have a substituent; and T1 represents a carbonyl group or the like] and a medicament comprising the same. The compound has strong FXa inhibitory action, provides prompt, sufficient and long-lasting anti-thrombus effects when orally administered, and has low side effects and is therefore useful as an excellent anticoagulant.

  本发明涉及一种磺酰基衍生物，其由以下式（I）表示：Q1-Q2-T1-Q3-SO2-QA（I）[其中，Q1代表饱和或不饱和的5-或6-成员环烃基，5-或6-成员杂环基，二环融合环或三环融合环基，可以有取代基；Q2代表单键，氧原子，硫原子，线性或支链C1-6烷基或类似物；QA代表芳基烯基，可以有取代基，或杂环芳基烯基，可以有取代基；T1代表羰基或类似物]，以及包含该化合物的药物。该化合物具有强烈的FXa抑制作用，在口服时提供迅速，充分和持久的抗血栓效果，并且副作用低，因此是一种优秀的抗凝剂。
• US6747023B1
  申请人：——

  公开号：US6747023B1

  公开（公告）日：2004-06-08
• Design, synthesis, and biological activity of non-basic compounds as factor Xa inhibitors: SAR study of S1 and aryl binding sites
  作者：Satoshi Komoriya、Noriyasu Haginoya、Shozo Kobayashi、Tsutomu Nagata、Akiyoshi Mochizuki、Masanori Suzuki、Toshiharu Yoshino、Haruhiko Horino、Takayasu Nagahara、Makoto Suzuki、Yumiko Isobe、Taketoshi Furugoori

  DOI：10.1016/j.bmc.2005.04.006

  日期：2005.6

  Compound 7 was identified as the active metabolite of 6 by HPLC and mass spectral analysis. Modification of lead compound 7 by transformation of its N-oxide 6-6 biaryl ring system and fused aromatics produced a series of non-basic fxa inhibitors with excellent potency in anti-fXa and anticoagulant assays. The optimized compounds 73b and 75b showed sub to one digit micromolar anticoagulant activity (PTCT2). Particularly, anti-fXa activity was detected in plasma of rats orally administered with 1 mg/kg of compound 75b. (c) 2005 Elsevier Ltd. All rights reserved.