1-<4-(benzyloxy)benzoyl>-2-(cyanoethyl)hydrazine | 147807-60-1

• 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: 1-<4-(benzyloxy)benzoyl>-2-(cyanoethyl)hydrazine
• 英文别名: 4-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide；4-benzyloxy-N'-2-cyanoethylbenzohydrazide；4-(benzyloxy)benzoic acid N'-2-cyanoethyl hydrazide；1-(4-benzyloxy benzoyl) 2-(2-cyano ethyl) hydrazine；N'-(2-cyanoethyl)-4-phenylmethoxybenzohydrazide
• CAS: 147807-60-1
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: YOYOMPCHZRRTGS-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  488.8±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<4-(benzyloxy)benzoyl>-2-(cyanoethyl)hydrazine 在 四氯化碳 、 18-冠醚-6 、 三苯基膦 、 cesium fluoride 作用下， 以 甲苯 、 乙腈 为溶剂， 20.0~25.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 生成 3-[2-氧代-5-[4-(苯基甲氧基)苯基]-1,3,4-恶二唑-3-基]丙腈
  参考文献：
  名称：

  腈与二氧化碳的1,3-偶极环加成反应：获得1,3,4-Oxadiazole-2（3H）-ones

  摘要：

  通过CsF / 18-crown-6介导的腈亚胺的1,3-偶极环加成和2.0 MPa的CO2，可以实现1,3,4-恶二唑-2（3H）-1的高效合成。CsF / 18-crown-6在增强CO2作为1,3-偶极亲子的反应中起着关键作用。这种无过渡金属的方法对1,3,4-恶二唑-2（3H）-one的实际应用通过方便地合成市售除草剂Oxadiazon和MAO B抑制剂得到了强调。

  DOI：

  10.1021/acs.joc.7b00963
• 作为产物：
  描述：

  4-苄氧基苯甲酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 77.0h， 生成 1-<4-(benzyloxy)benzoyl>-2-(cyanoethyl)hydrazine
  参考文献：
  名称：

  某些酰肼及其类似物的合成及其体外杀菌作用。

  摘要：

  通过用水合肼处理不同的酯来合成二十一个酰肼。通过用烷基/芳基/酰基卤化物处理酰肼得到取代的酰肼。这些化合物中的某些表现出潜在的体外杀菌作用。所有合成化合物的结构通过光谱分析确认。

  DOI：

  10.1016/s0968-0896(02)00611-9

文献信息

• Aryl substituted tetrazole derivatives, and application thereof in
  申请人：Delalande S.A.

  公开号：US05100910A1

  公开（公告）日：1992-03-31

  Compounds for therapeutic use of formula: ##STR1## where the chain--W--V--N--represents--N.dbd.N--N--, --N--N.dbd.N--, --O--CO--N--, --O--CS--N--, --S--CO--N-- or --S--CS--N--; Ar is an aryl group; and A is a vinyl group or an alkylene chain terminated by CN, methoxy, ethoxy, OH, halogen or NH.sub.2 which may possibly be substituted.

  用于治疗配方的化合物：##STR1## 其中链-W--V--N--代表--N.dbd.N--N--, --N--N.dbd.N--, --O--CO--N--, --O--CS--N--, --S--CO--N--或--S--CS--N--; Ar是芳基团；A是乙烯基团或由CN、甲氧基、乙氧基、OH、卤素或NH.sub.2终止的烯烃链，可能被取代。
• .BETA.-N-Cyanoethyl Acyl Hydrazide Derivatives: A New Class of .BETA.-Glucuronidase Inhibitors.
  作者：Khalid Mohammed Khan、Shahida Shujaat、Shagufta Rahat、Safdar Hayat、Atta-ur-Rahman、Muhammad Iqbal Choudhary

  DOI：10.1248/cpb.50.1443

  日期：——

  Eight new β-N-substituted acyl hydrazides along with their corresponding acyl derivatives were synthesized and screened for in vitro β-glucuronidase inhibition and found to be active against the enzyme. All of these compounds were found to be noncompetitive inhibitors except for N′-(2-cyanoethyl)-4-hydroxy benzohydrazide (10), which was found to be an uncompetitive inhibitor. Structure–activity relationship studies indicated that the benzyloxy group present in compounds 12 and 13 is responsible for the β-glucuronidase inhibition activity.

  合成了八种新的β-N-取代酰肼及其相应的酰基衍生物，并对它们进行了体外β-葡萄糖苷酶抑制活性筛选，发现它们对酶具有活性。除了N'-(2-氰乙基)-4-羟基苯甲酼肼（10）被发现是非竞争性抑制剂外，所有这些化合物都被发现是非竞争性抑制剂。结构-活性关系研究表明，化合物12和13中的苄氧基是导致β-葡萄糖苷酶抑制活性的原因。
• New (hetero)aryl substituted diazole derivatives, the method of
  申请人：Delalande S.A.

  公开号：US05250551A1

  公开（公告）日：1993-10-05

  Compounds for therapeutic use of formula: ##STR1## where the chain--W--V--N--represents--N.dbd.N--N--, --N--N.dbd.N--,--O--CO--N--,--O--CS--N--, --S--CO--N--or--S--CS--N--; Ar is an aryl group; and A is a vinyl group or an alkylene chain terminated by CN, methoxy, ethoxy, OH, halogen or NH.sub.2 which may possibly be substituted.

  用于治疗的化合物公式为：##STR1## 其中链-W-V-N-表示-N.dbd.N--N--，--N--N.dbd.N--，--O--CO--N--，--O--CS--N--，--S--CO--N--或--S--CS--N--；Ar是芳基基团；A是乙烯基或由CN、甲氧基、乙氧基、OH、卤素或NH.sub.2终止的烷基链，可能会被取代。
• 5-[4-(Benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives and related analogs: new reversible, highly potent, and selective monoamine oxidase type B inhibitors
  作者：Fathi Mazouz、Salah Gueddari、Claude Burstein、Daniel Mansuy、Rene Milcent

  DOI：10.1021/jm00061a006

  日期：1993.4

  Thirty-three new 5-[4-(benzyloxy)phenyl]-1,3,4-oxadiazol-2(3H)-one derivatives including related analogues, designed as inhibitors of monoamine oxidase type B (MAO B), were synthesized and investigated both in vitro and ex vivo for their abilities to inhibit selectively rat brain MAO B over MAO A. Three inhibitors were found to act as reversible, highly potent, and selective MAO B inhibitors, namely the nitrile derivative 5-[4-(benzyloxy)phenyl]-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one (12a) and two closely related homologues, the corresponding oxadiazolethione 13a and the alcohol 14b. Their IC50(MAO B) values are in the low nanomolar range of 1.4-4.6 nM and their selectivities, estimated by the ratio of IC50 values (A/B), are from 3200 to >71 400. Compound 12a exhibited the highest activity against MAO B. Its IC50 was evaluated to be 1.4 nM with a quasitotal selectivity (>71 400) toward this enzyme. In ex vivo studies, 12a showed a reversible and short duration of action. MAO B was markedly inhibited with the oral dose of 1 mg/kg without any alteration of MAO A, and the inhibition almost did not exceed 24 h. Its ED50 (1 h after oral administration) was evaluated to be 0.56 mg (1.7 mumol)/kg. Remarkably, MAO A was not affected at doses as high as 1500 mg/kg, po. In addition, no apparent toxicity or behavioral anomaly was observed during the treatment even at the maximum administrated dose. SAR studies emphasize the existence of three binding sites to the enzyme with a special importance of the terminal phenyl. Analysis of the inhibition kinetics indicated that 12a acts in a two-step mechanism as a competitive, slow, and tight-binding inhibitor of MAO B with a K(i) value of 0.22 muM and an overall K(i)* value at equilibrium of 0.7 nM.
• Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates
  作者：Khalid Mohammed Khan、Shagufta Rahat、Muhammad Iqbal Choudhary、Atta-ur-Rahman、Usman Ghani、Shahnaz Perveen、Shagufta Khatoon、Ahsana Dar、Abdul Malik

  DOI：10.1002/1522-2675(200202)85:2<559::aid-hlca559>3.0.co;2-a

  日期：2002.2

  To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates I and 2 were substituted with p-toluenesulfonyl ( --> 4 and 5), benzoyl ( 6 and 7), and benzyl groups ( 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12,24,28, and 29 appreciable antifungal activities. Compound 7 inhibits a-chymotrypsin.