3,3-bis(4-fluorophenyl)-2-propen-1-amine | 144477-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-bis(4-fluorophenyl)-2-propen-1-amine
• 英文别名: 3,3-Di(4-fluorophenyl)-2-propenyl amine；3,3-bis(4-fluorophenyl)prop-2-en-1-amine
• CAS: 144477-59-8
• 化学式: C₁₅H₁₃F₂N
• 分子量: 245.272
• InChiKey: RRHLLNRHSLZPNU-UHFFFAOYSA-N

物化性质

• 沸点：
  358.1±42.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-fluoro-4-methylsulfonylaminophenyl)propionic acid 、 3,3-bis(4-fluorophenyl)-2-propen-1-amine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到SH-135
  参考文献：
  名称：

  2-(4-Methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure–activity relationships in the B and C-regions

  摘要：

  On the basis of the previous lead N-4-t-butylbenzyl 2-(3-fluoro-4-methylsulfonylaminophenyl) propanamide (3) as a potent TRPV1 antagonist, structure-activity relationships for the B (propanamide part) and C-region (4-t-butylbenzyl part) have been investigated for rTRPV1 in CHO cells. The B-region was modified with dimethyl, cyclopropyl and reverse amides and then the C-region was replaced with 4-substituted phenyl, aryl alkyl and diaryl alkyl derivatives. Among them, compound 50 showed high binding affinity with K-i = 21.5 nM, which was twofold more potent than 3 and compound 54 exhibited potent antagonism with K-i(ant) = 8.0 nM comparable to 3. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.014
• 作为产物：
  描述：

  4,4'-二氟二苯甲酮 在 lithium aluminium tetrahydride 、 sodium ethanolate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 5.5h， 生成 3,3-bis(4-fluorophenyl)-2-propen-1-amine
  参考文献：
  名称：

  Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups

  摘要：

  Analogues of the potent histamine H-2 agonist arpromidine, characterized by non-heterocyclic groups (phenyl, cyclo-hexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H-2 agonistic and H-1 antagonistic activity in the isolated guinea pig right atrium and ileum, respectively. In the diphenylpropylguanidine series an increase in H-2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 less-than-or-equal-to 7.75 vs pD2 = 7.15 for the unsubstituted parent compound). Compounds chlorinated at both phenyl rings were considerably less potent. Highest combined H-2 agonistic/H-1 antagonistic potency was found in the 4-fluorophenyl series. The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium. The H-1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series. Thus, aromatic rings appear not to be required for high H-2 agonistic potency but are useful for combined H-2 agonistic/H-1 antagonistic activity.

  DOI：

  10.1016/0223-5234(92)90145-q

文献信息

• [EN] 4-(METHYL SULFONYL AMINO) PHENYL ANALOGUES AS VANILLOID ANTAGONIST SHOWING EXCELLENT ANALGESIC ACTIVITY AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME<br/>[FR] ANALOGUES DE 4-(METHYL SULFONYL AMINO)PHENYLE UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR VANILLOIDE AYANT UNE EXCELLENTE ACTIVITE ANALGESIQUE, ET COMPOSITIONS PHARMACEUTIQUE LES COMPRENANT
  申请人：DIGITALBIOTECH CO LTD

  公开号：WO2005003084A1

  公开（公告）日：2005-01-13

  The present invention relates to novel 4-(methylsulfonylamino) phenyl analogue as a potent vanilloid receptor antagonist and the pharmaceutical compositions comprising the same. The inventive compound can be useful for analgesics to prevent, alleviate or treat pain diseases or inflammatory disease comprising pain, acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflammatory bowel disease, inflammatory disease and urgent urinary incontinence.

  本发明涉及一种新型的4-(甲磺胺基)苯基类似物，作为有效的辣椒素受体拮抗剂，以及包含该类似物的药物组合物。这种创新化合物可用于镇痛药，用于预防、缓解或治疗疼痛疾病或包括疼痛的炎症性疾病，如急性疼痛、慢性疼痛、神经痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病性神经病、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、哮喘或慢性阻塞性肺疾病等呼吸道疾病、皮肤、眼睛或粘膜的刺激、发热、胃十二指肠溃疡、炎症性肠病、炎症性疾病和急性尿失禁。
• 4-(Methyl sulfonyl amino) phenyl analogues as vanilloid antagonist showing excellent analgesic activity and the pharmaceutical compositions comprising the same
  申请人：Lee Woo Jee

  公开号：US20060258884A1

  公开（公告）日：2006-11-16

  4-(methylsulfonylamino)phenyl analogues as potent vanilloid receptor antagonists and pharmaceutical compositions comprising the same. The compounds are useful as analgesics to prevent, alleviate or treat pain diseases or inflammatory disease including pain, acute pain, chronic pain, neuropathic pain, post-operative pain, migraine, arthralgia, neuropathies, nerve injury, diabetic neuropathy, neurodegeneration, neurotic skin disorder, stroke, urinary bladder hypersensitiveness, irritable bowel syndrome, a respiratory disorder such as asthma or chronic obstructive pulmonary disease, irritation of skin, eye or mucous membrane, fervescence, stomach-duodenal ulcer, inflammatory bowel disease, inflammatory disease and urgent urinary incontinence.

  4-(甲基磺酰氨基)苯类似物作为有效的vanilloid受体拮抗剂和包含它们的制药组合物。这些化合物可用作镇痛剂，以预防、缓解或治疗疼痛疾病或炎症性疾病，包括疼痛、急性疼痛、慢性疼痛、神经病性疼痛、术后疼痛、偏头痛、关节痛、神经病、神经损伤、糖尿病神经病变、神经退行性疾病、神经性皮肤疾病、中风、膀胱过敏、肠易激综合征、呼吸系统疾病，如哮喘或慢性阻塞性肺病、皮肤、眼睛或黏膜刺激、发热、胃十二指肠溃疡、炎症性肠病、炎症性疾病和紧急的尿失禁。
• 4-(METHYL SULFONYL AMINO) PHENYL ANALOGUES AS VANILLOID ANTAGONIST SHOWING EXCELLENT ANALGESIC ACTIVITY AND THE PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Grünenthal GmbH

  公开号：EP1658265A1

  公开（公告）日：2006-05-24
• EP1658265A4
  申请人：——

  公开号：EP1658265A4

  公开（公告）日：2006-11-29
• US8642657B2
  申请人：——

  公开号：US8642657B2

  公开（公告）日：2014-02-04