3-(5-nitro-1H-indol-3-yl)cyclohexanone | 1152478-65-3

• 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: 3-(5-nitro-1H-indol-3-yl)cyclohexanone
• 英文别名: (+/-)-3-(5-nitro-1H-indol-3-yl)cyclohexanone；3-(5-nitro-1H-indol-3-yl)cyclohexan-1-one
• CAS: 1152478-65-3
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: LNULIIPCSKKNOC-UHFFFAOYSA-N

物化性质

• 沸点：
  503.7±50.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(5-nitro-1H-indol-3-yl)cyclohexanone 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 为溶剂， 生成 tert-butyl methyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate
  参考文献：
  名称：

  First-in-Class, Dual-Action, 3,5-Disubstituted Indole Derivatives Having Human Nitric Oxide Synthase (nNOS) and Norepinephrine Reuptake Inhibitory (NERI) Activity for the Treatment of Neuropathic Pain

  摘要：

  A family of different 3,5-disubstituted indole derivatives having 6-membered rings were designed, synthesized, and demonstrated inhibition of human nitric oxide synthase (NOS) with norepinephrine reuptake inhibitory activity (NERO. The structure-activity relationship (SAR) within the cyclohexane ring showed the cis-isomers to be more potent for neuronal NOS and selective over endothelial NOS compared to their trans-counterparts. Compounds, such as cis-(+)-37, exhibited dual nNOS and NET inhibition (IC50 of 0.56 and 1.0 mu M, respectively) and excellent selectivity (88-fold and 12-fold) over eNOS and iNOS, respectively. The lead compound (cis-(+)-37) showed lack of any direct vasoconstriction or inhibition of ACh-mediated vasorelaxation in isolated human coronary arteries. Additionally, cis-(+)-37 was effective at reversing both allodynia and thermal hyperalgesia in a standard Chung (spinal nerve ligation) rat neuropathic pain model. Overall, the data suggest that cis-(+)-37 is a promising dual action development candidate having therapeutic potential for the treatment of neuropathic pain.

  DOI：

  10.1021/jm300138g
• 作为产物：
  描述：

  2-环己烯-1-酮 、 5-硝基吲哚 在 bismuth(III) nitrate 作用下， 以 乙腈 为溶剂， 以41%的产率得到3-(5-nitro-1H-indol-3-yl)cyclohexanone
  参考文献：
  名称：

  3,5 - SUBSTITUTED INDOLE COMPOUNDS HAVING NOS AND NOREPINEPHRINE REUPTAKE INHIBITORY ACTIVITY

  摘要：

  本发明涉及具有一氧化氮合酶（NOS）抑制活性以及对去甲肾上腺素转运蛋白（NET）具有抑制活性的新型3,5-取代吲哚化合物（I）的公式，以及含有它们的药用和诊断组合物，以及它们的医疗用途。

  公开号：

  US20090131503A1

文献信息

• [EN] INDOLE COMPOUNDS AND METHODS FOR TREATING VISCERAL PAIN<br/>[FR] COMPOSÉS D'INDOLE ET PROCÉDÉS DE TRAITEMENT DE LA DOULEUR VISCÉRALE
  申请人：NEURAXON INC

  公开号：WO2009062319A1

  公开（公告）日：2009-05-22

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  该发明涉及治疗哺乳动物体内因一氧化氮合酶（NOS）或5-羟色胺受体5HT1D/1B的作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者施用式(I)的吲哚化合物的治疗有效量，或其药学上可接受的盐或前药。该发明的方法还可以包括额外治疗剂的施用。该发明还涉及式(I)的新化合物、其药物组合物以及解决对映体混合物的方法。
• Indole compounds and methods for treating visceral pain
  申请人：Maddaford Shawn

  公开号：US08673909B2

  公开（公告）日：2014-03-18

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  该发明涉及治疗哺乳动物体内由一氧化氮合酶（NOS）或5-羟色胺5HT1D / 1B受体作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者施用式（I）的吲哚化合物或其药学上可接受的盐或前药的治疗有效量。该发明的方法还可以进一步包括给予额外的治疗剂量。该发明还涉及式（I）的新化合物、其药物组成物以及解决对映体混合物的方法。
• INDOLE COMPOUNDS AND METHODS FOR TREATING VISCERAL PAIN
  申请人：Maddaford Shawn

  公开号：US20090192157A1

  公开（公告）日：2009-07-30

  The invention features methods of treating visceral pain or a condition in a mammal caused by the action of nitric oxide synthase (NOS) or by the action of serotonin 5HT1D/1B receptors, by administering to a patient in need thereof a therapeutically effective amount of an indole compound of Formula (I), or a pharmaceutically acceptable salt or prodrug thereof. The methods of the invention may further comprise the administration of additional therapeutic agent. The invention also features new compounds of Formula (I), pharmaceutical compositions thereof, and methods of resolving enantiomeric mixtures.

  本发明涉及一种治疗哺乳动物因一氧化氮合酶（NOS）或血清素5HT1D/1B受体作用引起的内脏疼痛或疾病的方法，通过向需要治疗的患者投与公式（I）的吲哚化合物或其药学上可接受的盐或前药的治疗有效量。本发明的方法可能进一步包括给予额外的治疗药物。本发明还涉及公式（I）的新化合物、其制药组合物以及解决对映体混合物的方法。
• 3,5-SUBSTITUTED INDOLE COMPOUNDS HAVING NOS AND NOREPINEPHRINE REUPTAKE INHIBITORY ACTIVITY
  申请人：Neuraxon, INC.

  公开号：EP2220074A1

  公开（公告）日：2010-08-25
• US8673909B2
  申请人：——

  公开号：US8673909B2

  公开（公告）日：2014-03-18