3,3-二苯基丙肼 | 58973-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,3-二苯基丙肼
• 英文名称: 3,3-diphenylpropionic acid hydrazide
• 英文别名: β.β-Diphenyl-propionsaeure-hydrazid；3,3-Diphenyl-propionsaeure-hydrazid；3,3-diphenylpropanohydrazide；3,3-diphenylpropanehydrazide
• CAS: 58973-41-4
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD01722175
• 分子量: 240.305
• InChiKey: CHQPMMMDWSZFDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-isothiocyanatobutyric acid 、 3,3-二苯基丙肼 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  4-烷基-1,2,4-三唑-3-硫酮类似物作为金属-β-内酰胺酶抑制剂

  摘要：

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如

  DOI：

  10.1016/j.bioorg.2021.105024
• 作为产物：
  描述：

  3,3-二苯丙酸乙酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3,3-二苯基丙肼
  参考文献：
  名称：

  Syntheses and anti-inflammatory and analgesic activities of hydroxamic acids and acid hydrazides.

  摘要：

  根据普遍接受的观点，铜离子参与了炎症的发生，因此合成了来自各种取代肉桂酸和氢肉桂酸的羟肟酸和酸肼，期望它们能与铜离子形成配位化合物，并通过卡拉胶诱导的大鼠爪肿胀实验评估其抗炎活性，通过苯醌扭动法评估其镇痛活性。部分合成的化合物表现出这两种活性，3-(3, 4-二甲氧基苯基)丙氢羟肟酸及其锌配合物的活性超过阿司匹林。羟肟酸衍生物的铜(II)配合物被合成，并根据元素分析、分子量测定和磁性测试结果推测其具有聚合结构。

  DOI：

  10.1248/cpb.31.2810

文献信息

• [EN] 5-SUBSTITUTED 2-(PHENYLMETHYL) THIO-4-PHENYL-4H-1,2,4-TRIAZOLE DERIVATIVES AND RELATED COMPOUNDS AS GABA-AGONISTS FOR THE TREATMENT OF URINARY INCONTINENCE AND RELATED DISEASES<br/>[FR] DERIVES DE 2-(PHENYLMETHYL)THIO-4-PHENYL-4H-1,2,4-TRIAZOLE SUBSTITUES EN 5 ET COMPOSES ASSOCIES UTILISES EN TANT QUE GABA-AGONISTES DANS LE TRAITEMENT DE L'INCONTINENCE URINAIRE ET DES MALADIES ASSOCIEES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2005039569A1

  公开（公告）日：2005-05-06

  This invention relates to phenyltriazole derivatives of the formula (I) and salts thereof which is useful as an active ingredient of pharmaceutical preparations : (I) wherein R1 represents alkyl optionally substituted or 3-8 membered saturated or unsaturated ring optionally substituted, R2 represents -COR21, -(CH2)n-R21 or tert-butyl, X represents CR10R11, NR12, S, O, SO2, or SO wherein R10, R11 and R12 independently represent hydrogen or methyl. The other substituents are as defined in the claims. The phenyltriazole derivatives of the present invention have an excellent activity as GABAb agonist and are useful for the prophylaxis and treatment of diseases associated with GABAb activity, in particular for the treatment of overactive bladder, urinary incontinence such as urge urinary incontinence, benign prostatic hyperplasia (BPH), chronic pain, neuropathic pain, postoperative pain, rheumatoid arthritic pain, neuralgia, neuropathies, algesia, or nerve injury.

  本发明涉及式(I)的苯基三唑衍生物及其盐，其作为药物制剂的活性成分：（I）其中R1代表烷基，可选择地取代或3-8成员饱和或不饱和环，可选择地取代，R2代表-COR21，-(CH2)n-R21或叔丁基，X代表CR10R11，NR12，S，O，SO2或SO其中R10，R11和R12独立地代表氢或甲基。其他取代基如权利要求中所定义。本发明的苯基三唑衍生物具有出色的GABAb激动剂活性，并且可用于预防和治疗与GABAb活性相关的疾病，特别是用于治疗过度活动膀胱，尿失禁，如急迫性尿失禁，前列腺增生（BPH），慢性疼痛，神经痛，术后疼痛，类风湿关节炎疼痛，神经痛，神经病，疼痛或神经损伤。
• 1,2,4‐Triazole‐3‐Thione Analogues with a 2‐Ethylbenzoic Acid at Position 4 as VIM‐type Metallo‐β‐Lactamase Inhibitors
  作者：Federica Verdirosa、Laurent Gavara、Laurent Sevaille、Giusy Tassone、Giuseppina Corsica、Alice Legru、Georges Feller、Giulia Chelini、Paola Sandra Mercuri、Silvia Tanfoni、Filomena Sannio、Manuela Benvenuti、Giulia Cerboni、Filomena De Luca、Ezeddine Bouajila、Yen Vo Hoang、Patricia Licznar‐Fajardo、Moreno Galleni、Cecilia Pozzi、Stefano Mangani、Jean‐Denis Docquier、Jean‐François Hernandez

  DOI：10.1002/cmdc.202100699

  日期：2022.4.5

  AbstractMetallo‐β‐lactamases (MBLs) are increasingly involved as a major mechanism of resistance to carbapenems in relevant opportunistic Gram‐negative pathogens. Unfortunately, clinically efficient MBL inhibitors still represent an unmet medical need. We previously reported several series of compounds based on the 1,2,4‐triazole‐3‐thione scaffold. In particular, Schiff bases formed between diversely 5‐substituted‐4‐amino compounds and 2‐carboxybenzaldehyde were broad‐spectrum inhibitors of VIM‐type, NDM‐1 and IMP‐1 MBLs. Unfortunately, these compounds were unable to restore antibiotic susceptibility of MBL‐producing bacteria, probably because of poor penetration and/or susceptibility to hydrolysis. To improve their microbiological activity, we synthesized and characterized compounds where the hydrazone‐like bond of the Schiff base analogues was replaced by a stable ethyl link. This small change resulted in a narrower inhibition spectrum, as all compounds were poorly or not inhibiting NDM‐1 and IMP‐1, but showed a significantly better activity on VIM‐type enzymes, with Ki values in the μM to sub‐μM range. The resolution of the crystallographic structure of VIM‐2 in complex with one of the best inhibitors yielded valuable information about their binding mode. Interestingly, several compounds were shown to restore the β‐lactam susceptibility of VIM‐type‐producing E. coli laboratory strains and also of K. pneumoniae clinical isolates. In addition, selected compounds were found to be devoid of toxicity toward human cancer cells at high concentration, thus showing promising safety.
• Sieglitz, Chemische Berichte, 1922, vol. 55, p. 2042
  作者：Sieglitz

  DOI：——

  日期：——
• TANAKA, KUNIYOSHI;MATSUO, KEIZO;NAKANISHI, AI;HATANO, TOSHIKO;IZEKI, HISA+, CHEM. AND PHARM. BULL., 1983, 31, N 8, 2810-2819
  作者：TANAKA, KUNIYOSHI、MATSUO, KEIZO、NAKANISHI, AI、HATANO, TOSHIKO、IZEKI, HISA+

  DOI：——

  日期：——
• 5-SUBSTITUTED 2-(PHENYLMETHYL)THIO-4-PHENYL-4H-1,2,4-TRIAZOLE DERIVATIVES AND RELATED COMPOUNDS AS GABA-AGONISTS FOR THE TREATMENT OF URINARY INCONTINENCE AND RELATED DISEASES
  申请人：Bayer HealthCare AG

  公开号：EP1677786A1

  公开（公告）日：2006-07-12