(6-chlorobenzo[b]furan-2-yl)sulfonyl chloride | 259807-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (6-chlorobenzo[b]furan-2-yl)sulfonyl chloride
• 英文别名: 6-chloro-1-benzofuran-2-sulfonyl chloride；6-Chlorobenzo[b]furan-2-sulfonyl chloride
• CAS: 259807-32-4
• 化学式: C₈H₄Cl₂O₃S
• 分子量: 251.09
• InChiKey: CFZKYRDHFFOASQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-chlorobenzo[b]furan-2-yl)sulfonyl chloride 、 (3S)-3-amino-1-[(1S)-1-methyl-2-(morpholin-4-yl)-2-oxoethyl]pyrrolidin-2-one 以44%的产率得到6-chloro-N-[(3S)-1-[(2S)-1-(morpholin-4-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]-1-benzofuran-2-sulfonamide
  参考文献：
  名称：

  Factor Xa Inhibitors:  S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides

  摘要：

  Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.

  DOI：

  10.1021/jm060870c
• 作为产物：
  描述：

  6-氯-1-苯并呋喃 在 叔丁基锂 、 二氧化硫 、 N-氯代丁二酰亚胺 作用下， 以 乙醚 、 正戊烷 、 二氯甲烷 为溶剂， 反应 8.0h， 以64%的产率得到(6-chlorobenzo[b]furan-2-yl)sulfonyl chloride
  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。
• CHOLESTEROL BIOSYNTHESIS INHIBITORS CONTAINING AS THE ACTIVE INGREDIENT TRICYCLIC SPIRO COMPOUNDS
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP1346994A1

  公开（公告）日：2003-09-24

  This invention relates to a cholesterol biosynthesis inhibiting drug by including a tricyclic compounds having spiro union represented by the following formula (I) or its salt as an ingredient, which can be administered orally and which exhibits potent serum cholesterol decreasing action. In the formula, A is a 5-, 6-membered cyclic hydrocarbon group, or the like; B is a single bond, a carbonyl group, or the like; D is a hydrogen atom, or the like; X is a nitrogen atom or the like; Y is an oxygen atom, -NH-, or the like; Z is a methylene group, a carbonyl group, or the like; T is -S(O)z-, a carbonyl group, or the like; Q is a hydrocarbon group, a heterocyclic group, or the like;    l, m and n are independently an integer selected from 0-2 with the proviso that 1 and m are not simultaneously 0; and r is an integer of 0 or 1.

  本发明涉及一种抑制胆固醇生物合成的药物，其成分包括具有下式（I）所代表的螺联的三环化合物或其盐，可口服给药，具有强效降低血清胆固醇的作用。 式中，A 是 5、6 元环状烃基或类似物；B 是单键、羰基或类似物；D 是氢原子或类似物；X 是氮原子或类似物；Y 是氧原子、-NH- 或类似物；Z 是亚甲基、羰基或类似物；T 是-S(O)z-、羰基或类似物；Q 是烃基、杂环基或类似物； l、m 和 n 分别是选自 0-2 的整数，但 1 和 m 不能同时为 0；以及 r 是 0 或 1 的整数。
• US6747023B1
  申请人：——

  公开号：US6747023B1

  公开（公告）日：2004-06-08