5-(2-nitro-ethyl)-1H-indole | 87149-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(2-nitro-ethyl)-1H-indole
• 英文别名: 5-(2-nitroethyl)-1H-indole
• CAS: 87149-49-3
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: WDVRSQXNGVFUSU-UHFFFAOYSA-N

物化性质

• 沸点：
  407.5±28.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-nitro-ethyl)-1H-indole 在 铁粉 、 氯化铵 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 生成 1H-吲哚-5-乙胺
  参考文献：
  名称：

  4-Indolyl- N -hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in vitro and in vivo

  摘要：

  A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in vitro and in vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28 nM and 134 nM) and HDAC 2 (IC50 0.90 and 0.53 nM). N-Hydroxy-3-{4-[2-(1H-indo1-4-y1)-ethylsulfamoyl]-phenyl}-actylamide (13) inhibited the human cancer cell growth of PC3, A549, MDA-MB-231 and AsPC-1 with a GI(50) of 0.14, 0.25, 0.32, and 0.24 mu M, respectively. In in vivo evaluations bearing prostate PC3 xenografts nude mice model, compound 13 suppressed tumor growth with a tumor growth inhibition (TGI) of 62.2%. Immunohistochemistry of protein expressions, in PC-3 xenograft model indicated elevated acetyl-histone 3 and prominently inhibited HDAC2 protein expressions. Therefore, compound 13 could be a suitable lead for further investigation and the development of selective HDAC 2 inhibitors as potent anti-cancer compounds. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.079
• 作为产物：
  描述：

  5-吲哚甲醛 在 sodium tetrahydroborate 、 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 5-(2-nitro-ethyl)-1H-indole
  参考文献：
  名称：

  4-Indolyl- N -hydroxyphenylacrylamides as potent HDAC class I and IIB inhibitors in vitro and in vivo

  摘要：

  A series of 4,5-indolyl-N-hydroxyphenylacrylamides, as HDAC inhibitors, has been synthesized and evaluated in vitro and in vivo. 4-Indolyl compounds 13 and 17 functions as potent inhibitors of HDAC1 (IC50 1.28 nM and 134 nM) and HDAC 2 (IC50 0.90 and 0.53 nM). N-Hydroxy-3-{4-[2-(1H-indo1-4-y1)-ethylsulfamoyl]-phenyl}-actylamide (13) inhibited the human cancer cell growth of PC3, A549, MDA-MB-231 and AsPC-1 with a GI(50) of 0.14, 0.25, 0.32, and 0.24 mu M, respectively. In in vivo evaluations bearing prostate PC3 xenografts nude mice model, compound 13 suppressed tumor growth with a tumor growth inhibition (TGI) of 62.2%. Immunohistochemistry of protein expressions, in PC-3 xenograft model indicated elevated acetyl-histone 3 and prominently inhibited HDAC2 protein expressions. Therefore, compound 13 could be a suitable lead for further investigation and the development of selective HDAC 2 inhibitors as potent anti-cancer compounds. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.079

文献信息

• [EN] THERAPEUTIC HETEROCYCLIC COMPOUNDS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1991018897A1

  公开（公告）日：1991-12-12

  (EN) The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3; W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C1-4 alkyl, X is -O-, -S-, -NH-, or -CH2-, Y is oxygen or sulphur and the chiral centre (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions; and Z is a group of formula (iv), (v), or (vi), wherein R1 and R2 are independently selected from hydrogen and C1-4 alkyl and R3 is hydrogen or C1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.(FR) La présente invention se rapporte à des composés de formule (I) où n représente un nombre entier de 0 à 3; W représente un groupe de formule (i), (ii) ou (iii), où R représente hydrogène ou alkyle C1-4, X représente -O-, -S-, -NH-, ou -CH2-, Y représente oxygène ou soufre et le centre chiral (*) dans la formule (i) ou (ii) est dans sa forme (S) ou (R) ou représente un mélange de ceux-ci dans n'importe quelles proportions; et Z représente un groupe de formule (iv), (v) ou (vi) où R1 et R2 sont indépendamment sélectionnés à partir d'hydrogène et d'alkyle C1-4 et R3 représente hydrogène ou alkyle C1-4. L'invention décrit aussi des sels, des solvates et des dérivés physiologiquement fonctionnels de ces composés, ainsi que des procédés relatifs à leur préparation, des médicaments qui les contiennent et leur utilisation comme agents thérapeutiques, en particulier dans la prophylaxie et le traitement de la migraine.

  本发明涉及式(I)化合物，其中n为0至3的整数；W为式(i)、(ii)或(iii)的基团，其中R为氢或C1-4烷基，X为-O-、-S-、-NH-或-CH2-，Y为氧或硫，式(i)或(ii)中的手性中心(*)为其(S)或(R)形式或在任何比例下为它们的混合物；Z为式(iv)、(v)或(vi)的基团，其中R1和R2独立选择自氢和C1-4烷基，R3为氢或C1-4烷基；以及它们的盐、溶剂化物和生理功能衍生物，制备它们的方法，包含它们的药物以及它们在治疗中的使用，特别是在偏头痛的预防和治疗中。
• Indolyl tetrahydropyridines for treating migraine
  申请人：Burroughs Wellcome Co.

  公开号：US05399574A1

  公开（公告）日：1995-03-21

  ##STR1## The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3: W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulphur and the chiral center (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions: and Z is a group of formula (iv), (v), or (vi), wherein R.sup.1 and R.sup.2 are independently selected from hydrogen and C.sub.1-4 alkyl and R.sup.3 is hydrogen or C.sub.1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.

  本发明涉及式(I)的化合物，其中n是0到3的整数：W是式(i)、(ii)或(iii)的基团，其中R是氢或C.sub.1-4烷基，X是--O--、--S--、--NH--或--CH.sub.2--，Y是氧或硫，式(i)或(ii)中的手性中心(*)是其(S)或(R)形式或在任何比例下的混合物：Z是式(iv)、(v)或(vi)的基团，其中R.sup.1和R.sup.2独立地选自氢和C.sub.1-4烷基，R.sup.3是氢或C.sub.1-4烷基；以及它们的盐、溶剂化物和生理功能衍生物，其制备过程，含有它们的药物以及它们作为治疗剂的用途，特别是在偏头痛的预防和治疗中。
• Indolyl compounds for treating migraine
  申请人：Burroughs Wellcome Co.

  公开号：US05466699A1

  公开（公告）日：1995-11-14

  ##STR1## The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3: W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulphur and the chiral center (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions: and Z is a group of formula (iv), (v), or (vi), wherein R.sup.1 and R.sup.2 are independently selected from hydrogen and C.sub.1-4 alkyl and R.sup.3 is hydrogen or C.sub.1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.

  本发明涉及式(I)的化合物，其中n是0至3的整数：W是式(i)、(ii)或(iii)的基团，其中R是氢或C.sub.1-4烷基，X是--O--、--S--、--NH--或--CH.sub.2--，Y是氧或硫，式(i)或(ii)中的手性中心(*)为其(S)或(R)形式或在任何比例下为其混合物：Z是式(iv)、(v)或(vi)的基团，其中R.sup.1和R.sup.2独立选择自氢和C.sub.1-4烷基，而R.sup.3为氢或C.sub.1-4烷基；以及它们的盐、溶剂合物和生理功能衍生物，以及它们的制备方法、含有它们的药物和它们作为治疗剂的用途，特别是在偏头痛的预防和治疗中。
• 2-(Amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases
  申请人：Fleming E. Paul

  公开号：US20060040968A1

  公开（公告）日：2006-02-23

  A heterocyclic inhibitor having the formula I, with the variables defined herein, which is useful for treating inflammatory and other physiological disorders in which PKC-theta isoform plays a role:

  一种杂环抑制剂，具有以下公式I，其中变量在此定义，可用于治疗PKC-theta亚型在其中起作用的炎症和其他生理紊乱：
• Therapeutic heterocyclic compounds
  申请人：Zeneca Limited

  公开号：US05863935A1

  公开（公告）日：1999-01-26

  ##STR1## The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3: W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulphur and the chiral center (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions: and Z is a group of formula (iv), (v), or (vi), wherein R.sup.1 and R.sup.2 are independently selected from hydrogen and C.sub.1-4 alkyl and R.sup.3 is hydrogen or C.sub.1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.

  本发明涉及式（I）的化合物，其中n是0至3的整数：W是式（i），（ii）或（iii）的基团，其中R是氢或C.sub.1-4烷基，X是--O--，--S--，--NH--或--CH.sub.2--，Y是氧或硫，公式（i）或（ii）中的手性中心（*）以其（S）或（R）形式存在，或在任何比例下是其混合物：Z是式（iv），（v）或（vi）的基团，其中R.sup.1和R.sup.2独立地选自氢和C.sub.1-4烷基，R.sup.3是氢或C.sub.1-4烷基；以及它们的盐，溶剂合物和生理学上的功能衍生物，以及其制备方法，含有它们的药物和作为治疗剂的使用，特别是在偏头痛的预防和治疗中。