3-Methoxy-5-oxa-11-thia-benzo[a]fluoren-6-one | 54711-37-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-Methoxy-5-oxa-11-thia-benzo[a]fluoren-6-one
• 英文别名: 3-Methoxy-[1]benzothiolo[3,2-c]chromen-6-one
• CAS: 54711-37-4
• 化学式: C₁₆H₁₀O₃S
• 分子量: 282.32
• InChiKey: JCHPBWPBYZTABT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Methoxy-5-oxa-11-thia-benzo[a]fluoren-6-one 在 三氯化铝 、 二异丁基氢化铝 、 三乙胺 、 乙硫醇 作用下， 以 二氯甲烷 、 氯苯 、 甲苯 为溶剂， 反应 12.5h， 生成 tert-butyl-dimethyl-[(6-phenoxy-6H-[1]benzothiolo[3,2-c]chromen-3-yl)oxy]silane
  参考文献：
  名称：

  Synthesis and Pharmacology of Conformationally Restricted Raloxifene Analogues:  Highly Potent Selective Estrogen Receptor Modulators

  摘要：

  The 2-arylbenzothiophene raloxifene, 1, is a selective estrogen receptor modulator (SERM) which is currently under clinical evaluation for the prevention and treatment of postmenopausal osteoporosis. In vivo structure-activity relationships and molecular modeling studies have indicated that the orientation of the basic amine-containing side chain of 1, relative to the stilbene plane, is an important discriminating factor for the maintenance of tissue selectivity. We have constructed a series of analogues of 1 in which this side chain is held in an orientation which is orthogonal to the stilbene plane, similar to the low-energy conformation predicted for raloxifene. Herein, we report on the synthesis of these compounds and on their activity in a series of in vitro and in vivo biological assays reflective of the SERM profile. In particular, we describe their ability to (I) bind the estrogen receptor, (2) antagonize estrogen-stimulated proliferation of MCF-7 cells in vitro, (3) stimulate TGF-beta 3 gene expression in cell culture, (4) inhibit the uterine effects of ethynyl estradiol in immature rats, and (5) potently reduce serum cholesterol and protect against osteopenia in ovariectomized (OVX) rats without estrogen-like stimulation of uterine tissue. These data demonstrate that one of these compounds, LY357489, 4, is among the most potent SERMs described to date with in vivo efficacy on bone and cholesterol metabolism in OVX rats at doses as low as 0.01 mg/kg/d.

  DOI：

  10.1021/jm970688z
• 作为产物：
  描述：

  6a,11a-dihydro-6H-benzothieno<3,2-c><1>benzopyran-6-one 以66%的产率得到
  参考文献：
  名称：

  CONLEY R. A.; HEINDEL N. D., J. ORG. CHEM. , 1975, 40, NO 22, 3169-3173

  摘要：

  DOI：

文献信息

• 一种细菌抑制剂香豆素[3,4]并苯并噻吩类化 合物的制备方法
  申请人：诸暨市人民医院

  公开号：CN111440190B

  公开（公告）日：2021-08-24

  本发明公开了一种细菌抑制剂香豆素[3,4]并苯并噻吩类化合物的制备方法，制备方法为：式(Ⅰ)所示的2‑羟基肉桂醛类化合物、式(Ⅱ)所示的卤代苯类化合物和式(III)所示的单质硫，以溴化铁(FeBr3)为催化剂，乙醇水溶液(H2O‑EtOH＝1:1)为溶剂，1,8‑二氮杂二环十一碳‑7‑烯(DBU)为碱作用下充分反应，所述产物通过后处理制得香豆素[3,4]并苯并噻吩类化合物。本发明具有催化效率高、底物成本低廉、溶剂无毒低廉、对设备要求低、产率优良等优点。
• A nickel-catalyzed tandem reaction involving cyclic esterification/C–S bond formation for synthesizing 5-oxa-11-thia-benzofluoren-6-ones
  作者：Rongrong Cai、Qicai Wei、Runsheng Xu

  DOI：10.1039/d0ra04367b

  日期：——

  A nickel-catalyzed tandem reaction involving cyclic esterification/C–S bond formation has been developed. Starting from samples containing 3-(2-hydroxy-phenyl)-acrylic acids with 2-halide-benzenethiols, versatile biologically active 5-oxa-11-thia-benzofluoren-6-one compounds were efficiently synthesized in good to high yields. This new methodology provides an economical approach toward C–S bond formation

  已经开发了涉及环状酯化/C-S键形成的镍催化串联反应。从含有 3-(2-羟基-苯基)-丙烯酸和 2-卤化物-苯硫醇的样品开始，高效地合成了具有良好至高产率的多功能生物活性 5-oxa-11-thia-benzofluoren-6-one 化合物。这种新方法为 C-S 键的形成提供了一种经济的方法。
• Synthesis and antifungal activity of some 2-aryl-3-hydroxymethylbenzo[b]thiophenes
  作者：TAI Nakib、MJ Meegan、AM Looney、ML Burke

  DOI：10.1016/0223-5234(92)90031-u

  日期：1992.12

  This paper describes the preparation of a series of 2-aryl-3-hydroxymethylbenzo[b]thiophenes and 2-aryl-3-hydroxymethyl-2,3-dihydrobenzo[b]thiophenes. All of the products were examined for antifungal activity and many of the compounds displayed good activity against Cryptococcus neoformans, Torulopsis glabrata and Trichosporon cutaneum.
• Synthesis and Pharmacology of Conformationally Restricted Raloxifene Analogues:  Highly Potent Selective Estrogen Receptor Modulators
  作者：Timothy A. Grese、Lewis D. Pennington、James P. Sluka、M. Dee Adrian、Harlan W. Cole、Tina R. Fuson、David E. Magee、D. Lynn Phillips、Ellen R. Rowley、Pamela K. Shetler、Lorri L. Short、Murali Venugopalan、Na N. Yang、Masahiko Sato、Andrew L. Glasebrook、Henry U. Bryant

  DOI：10.1021/jm970688z

  日期：1998.4.1

  The 2-arylbenzothiophene raloxifene, 1, is a selective estrogen receptor modulator (SERM) which is currently under clinical evaluation for the prevention and treatment of postmenopausal osteoporosis. In vivo structure-activity relationships and molecular modeling studies have indicated that the orientation of the basic amine-containing side chain of 1, relative to the stilbene plane, is an important discriminating factor for the maintenance of tissue selectivity. We have constructed a series of analogues of 1 in which this side chain is held in an orientation which is orthogonal to the stilbene plane, similar to the low-energy conformation predicted for raloxifene. Herein, we report on the synthesis of these compounds and on their activity in a series of in vitro and in vivo biological assays reflective of the SERM profile. In particular, we describe their ability to (I) bind the estrogen receptor, (2) antagonize estrogen-stimulated proliferation of MCF-7 cells in vitro, (3) stimulate TGF-beta 3 gene expression in cell culture, (4) inhibit the uterine effects of ethynyl estradiol in immature rats, and (5) potently reduce serum cholesterol and protect against osteopenia in ovariectomized (OVX) rats without estrogen-like stimulation of uterine tissue. These data demonstrate that one of these compounds, LY357489, 4, is among the most potent SERMs described to date with in vivo efficacy on bone and cholesterol metabolism in OVX rats at doses as low as 0.01 mg/kg/d.
• CONLEY R. A.; HEINDEL N. D., J. ORG. CHEM. <JOCE-AH>, 1975, 40, NO 22, 3169-3173
  作者：CONLEY R. A.、 HEINDEL N. D.

  DOI：——

  日期：——