7-bromo-1,2-dihydronaphtho[2,1-b]furan | 337522-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 7-bromo-1,2-dihydronaphtho[2,1-b]furan
• 英文别名: 7-Bromo-1,2-dihydrobenzo[e][1]benzofuran
• CAS: 337522-15-3
• 化学式: C₁₂H₉BrO
• 分子量: 249.107
• InChiKey: NENZWAXOSPDTHM-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  366.1±11.0 °C(Predicted)
• 密度：
  1.558±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(1H-咪唑-5-基)-2-甲基丙烷-1-酮 、 7-bromo-1,2-dihydronaphtho[2,1-b]furan 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以48%的产率得到1-(1,2-Dihydronaphtho[2,1-b]furan-7-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
  参考文献：
  名称：

  C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors

  摘要：

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.016
• 作为产物：
  描述：

  6-Bromo-2-(2-propenyloxy)naphthalene 在 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.0h， 生成 7-bromo-1,2-dihydronaphtho[2,1-b]furan
  参考文献：
  名称：

  C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors

  摘要：

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.016

文献信息

• Imidazol-4-ylmehanols and their use as inhibitors of steroid C17-20 lyase
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06649643B1

  公开（公告）日：2003-11-18

  Imidazol-4-ylmethanols and their uses for preventing and treating primary tumors, metastasis and recurrence of tumors, various symptoms accompanying tumors, prostatic hypertrophy, virilism, hirsutism, male pattern alopecia, precocious puberty, endometriosis, uterine myoma, mastopathy and polycystic ovary syndrome are disclosed.

  Imidazol-4-ylmethanols及其用于预防和治疗原发性肿瘤、肿瘤转移和复发、伴随肿瘤的各种症状、前列腺肥大、男性化、多毛症、男性型脱发、性早熟、子宫内膜异位症、子宫肌瘤、乳腺病和多囊卵巢综合征的用途被披露。
• Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: synthesis of dihydrofuran derivatives
  作者：Zi-cong Chen、Lang Tong、Zhi-bo Du、Zhi-feng Mao、Xue-jing Zhang、Yong Zou、Ming Yan

  DOI：10.1039/c8ob00293b

  日期：——

  A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

  通过β-萘酚和4-羟基香豆素与乙烯基ulf盐的环化反应，开发了一种新的合成二氢呋喃衍生物的方法。在温和的条件下以中等至良好的产率制备了多种二氢呋喃衍生物。通过用DDQ脱氢，可以容易地将产物转化为相应的呋喃。
• IMIDAZOL-4-YLMETHANOLS USED AS INHIBITORS OF STEROID C17-20 LYASE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1222174B1

  公开（公告）日：2009-05-27
• US6649643B1
  申请人：——

  公开号：US6649643B1

  公开（公告）日：2003-11-18
• C17,20-lyase inhibitors. Part 2: Design, synthesis and structure–activity relationships of (2-naphthylmethyl)-1H-imidazoles as novel C17,20-lyase inhibitors
  作者：Nobuyuki Matsunaga、Tomohiro Kaku、Akio Ojida、Toshimasa Tanaka、Takahito Hara、Masuo Yamaoka、Masami Kusaka、Akihiro Tasaka

  DOI：10.1016/j.bmc.2004.06.016

  日期：2004.8

  A series of 1- and 4-(2-naphthylmethyl)-1H-imidazoles (3 and 4) has been synthesized and evaluated as C-17,C-20-lyase inhibitors. Several 6-methoxynaphthyl derivatives showed potent C-17,C-20-lyase inhibition, suppression of testosterone biosynthesis in rats and reduction in the weight of prostate and seminal vesicles in rats, whereas most of these compounds increased the liver weight after consecutive administrations. The effect on the liver weight was removed by incorporation of a hydroxy group and an isopropyl group at the methylene bridge, as seen in (S)-28d and (S)-42. Selectivity for C-17,C-20-lyase over 11beta-hydroxylase is also discussed, and (S)-42 was found to be a more than 260-fold selective inhibitor. Furthermore, (S)-42 showed a potent suppression of testosterone biosynthesis after a single oral administration in monkeys. These data suggest that (S)-42 may be a promising agent for the treatment of androgen-dependent prostate cancer. (C) 2004 Elsevier Ltd. All rights reserved.